Category: 173035-10-4

1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride, cas is 173035-10-4, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,173035-10-4

To a suspension of SIMes¡¤HCl (906mg, 2.64mmol) in THF (30mL) was added dropwise a 1.6M solution of n-butyl lithium in hexanes (1.65mL, 2.64mmol) at-78C with stirring. After 10min, the suspension was allowed to warm to room temperature for additional 10min. The mixture was cooled again to-78C and then treated with a cooled THF solution (-78C) of mesitylcopper (504mg including 0.09 equivalents of toluene, determined by 1H NMR, 2.64mmol) by means of a cannula. The reaction mixture was allowed to warm to room temperature and stirred for further 18h. The solvents were removed under reduced pressure. The resulting solid residue was dried for 2h and then extracted with toluene (50mL). The suspension was filtered through Kieselgur and the filter cake was washed with small portions of toluene (5mL). The resulting solution was concentrated under reduced pressure to 15mL and then stored at-18C for 18h while large colorless crystals were forming. The mother liquor was decanted from the crystals that were subsequently washed with cold toluene (5mL) and dried in vacuo for 15h. The mother liquor was combined with the washing solution, concentrated to 5mL and stored at-18C for about 3 weeks. From this solution a second crop of colorless crystals was isolated. Combined yield: 1.032g (2.11mmol, 80%). Anal. Calcd for C30H37N2Cu: C, 73.66; H, 7.62; N, 5.73. Found: C, 72.87; H, 7.91; N, 5.72. 1H NMR (500.13MHz, C6D6): delta 2.12 (s, 6H, p-CH3, NHC), 2.15 (s, 6H, o-CH3, CuMes), 2.18 (s, 12H, o-CH3, NHC), 2.26 (s, 3H, p-CH3, CuMes), 3.05 (s, 4H, CH2), 6.76 (s, 4H, CH, NHC), 6.86 (s, 2H, CH, CuMes). 13C NMR (125.77MHz, C6D6): delta 18.1 (o-CH3, NHC), 21.0 (p-CH3, NHC), 21.6 (p-CH3, CuMes), 28.0 (o-CH3, CuMes), 50.4 (CH2), 124.5 (CH, CuMes), 129.6 (CH, NHC), 132.7 (C, CuMes), 136.0, 136.2, 138.2 (3¡ÁC, Mes, NHC), 147.2 (C, CuMes), 163.7 (C, CuMes), 207.1 (C, CN2, NHC). MS (ESI in THF): m/z (rel. intensity)=675 (100) [(NHC)2Cu]+, 857 (34) [(NHC)2Cu2Mes]+; MS (ESI in CH3CN): m/z (rel. intensity)=764 (63) [(NHC)2Cu2(CN)]+, 675 (80) [(NHC)2Cu]+, 410 (42) [(NHC)Cu(CH3CN)]+, 397 (100) [(NHC)Cu(CO)]+, 369 (8) [(NHC)Cu]+, 307 (11) [(Mes)2(C3H4N2)+1]+. IR (KBr, cm-1): 3003, 2949, 2916, 2855, 2729, 2706, 1775, 1742, 1730, 1609, 1589, 1487, 1474, 1439, 1375, 1317, 1306, 1298, 1263, 1215, 1173, 1161, 1032, 1013, 951, 914, 883, 851, 839, 754, 741, 733, 721, 706, 689, 615, 602, 588, 573, 550, 532, 502, 482, 465, 419.

With the rapid development of chemical substances, we look forward to future research findings about 173035-10-4

Reference£º
Article; Stollenz, Michael; Fischer, Stefan; Gehring, Henrike; Resch, Stefan G.; Dechert, Sebastian; Grosse, Christian; Meyer, Franc; Journal of Organometallic Chemistry; vol. 821; (2016); p. 106 – 111;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.173035-10-4,1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride,as a common compound, the synthetic route is as follows.

Example 38 50.0g of 1,3-Bis-(2,4,6-trimethylphenyl)imidazolinium chloride was added to a 1000 mL single neck round bottom flask containing a Teflon-coated stirbar. 15.2 g of Lithium tert-butoxide (1.3 mol equivalents of Lithium tert-butoxide to 1,3-Bis-(2,4,6-trimethylphenyl)imidazolinium chloride) was added to the 1000 mL flask. 190 mL of anhydrous Hexanes was added to the 1000 mL flask and the flask was capped with a septum and the headspace was purged with argon for 15 minutes with stirring. This mixture was stirred for 2 hours at room temperature. After 2 hours the septum on the 1000 mL flask was replaced with a 250 mL addition funnel. 250 mL of CHCl3 was added to the addition funnel and the funnel was capped with a septum and purged with argon for 5 minutes. After the 250 mL of CHCl3 was added dropwise to the reaction mixture in the 1000 mL flask an additional 130 mL of CHCl3 was added to the addition funnel and the funnel was capped with a septum and purged with argon for 5 minutes. The additional 130 mL of CHCl3 was added dropwise to the reaction mixture in the 1000 mL flask with stirring. A total of 380 mL of CHCl3 was added dropwise to the 1000 mL flask at room temperature under an atmosphere of argon with stirring. Once the 380 mL of CHCl3 was added to the 1000 1 l flask the additional funnel was removed from the flask and the flask was capped with a septum. The headspace of the flask was purged with argon for 15 minutes. The reaction mixture was stirred for 24 hours under an atmosphere of argon to yield an off-white solution. This off-white solution is cooled to 0 C. and then washed with saturated NH4Cl(aq) (4*200 mL) in a separatory funnel at 22-25 C. The organic layer was then washed with saturated NaCl(aq) (2*200 mL) in a separatory funnel at 22-25 C. The organic layer was then placed in a single neck round bottom flask and the excess chloroform was removed in vacuo to yield the crude product as a powdery off-white solid. The off-white solid was washed with a minimal amount of cold methanol (0 C.) and filtered to give 52.5 g of 1,3-dimesityl-2-(trichloromethyl)imidazolidine (62.1 g theoretical yield) as a white to off-white crystalline powder in 85% yield.

The synthetic route of 173035-10-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Grubbs, Robert H.; Moore, Jason L.; Morgan, John P.; Bell, Andrew; US2003/83445; (2003); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.173035-10-4,1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride,as a common compound, the synthetic route is as follows.

Potassium 3-fluoronaphtho[1,8-cd][1,2,6]oxadiphosphinine-1(3H)-thiolate 1,3-disulfide (0.108 g,0.30 mmol) was dissolved in degassed water (10 mL). To this solution was added dropwise an equivalent amount of 1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride (0.102 g, 0.30 mmol) in water (10 mL). The precipitation was almost immediately formed and the mixture was allowed to continue stirring for 2 h. The precipitate was harvested by filtration and dissolved in dichloromethane(30 mL). The solution was dried over MgSO4 and dried in vacuo to give the title compound 15 as white foam (0.175 g, 93%). Selected IR (KBr, cm-1): 1628 (vs), 1481 (m), 1378 (m), 1261 (s), 1217 (m),1162 (m), 942 (s), 904 (m), 849 (m), 82 5(m), 769 (m), 691 (s), 643 (s), 585 (s). 1H-NMR (CD2Cl2, delta),8.61 (s, 2H, Ar-H), 8.32-7.34 (m, 6H, Ar-H), 7.00 (s, 2H, Ar-H), 4.49 (s, 1H, imidazol-H), 3.66 (t, 2H,CH2), 2.36 (s, 12H, CH3), 2.32 (s, 6H, CH3), 1.80 (t, 3H, CH2) ppm. 13C-NMR (CD2Cl2, delta), 159.7(imidazol-C ), 140.9 (Ar-C), 135.1 (Ar-C), 134.6 (Ar-C), 34.2 (Ar-C), 134.0 (Ar-C), 131.7 (Ar-C), 131.5(Ar-C), 130.3 (Ar-C), 130.1 (Ar-C), 129.6 (Ar-C), 126.5 (Ar-C), 126.3 (Ar-C), 125.1 (Ar-C), 124.9(Ar-C), 53.1 (imidazol-C), 51.8 (imidazol-C), 20.9 (CH3), 17.9 (CH3) ppm. 31P-NMR (CD2Cl2, delta),106.4 (d, 2J(P,P) = 54.0 Hz), 78.2 (dd, J(P,F) = 1101 Hz, 2J(P,P) = 54.0 Hz) pm. 19F-NMR (CD2Cl2, delta),-28.7 (dd, 1J(F,P) = 1100 Hz, 3J(P,F) = 3.3 Hz) ppm. MS (CI+, m/z), 307 [C21H27N2]+. Accurate massmeasurement (CI+MS): 307.2170 [C21H27N2]+, calculated mass for [C21H27N2]+: 307.2169; MS (CI-,m/z), 319 [C10H7FOP2S3]-. Accurate mass measurement (CI-MS): 318.9031 [C10H7FOP2S3]-, calculated mass for [C10H7FOP2S3]-: 318.9040.

173035-10-4 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride 2734917, achiral-catalyst compound, is more and more widely used in various.

Reference£º
Article; Hua, Guoxiong; Du, Junyi; Surgenor, Brian A.; Slawin, Alexandra M. Z.; Woollins, J. Derek; Molecules; vol. 20; 7; (2015); p. 12175 – 12197;,
Chiral Catalysts
Chiral catalysts – SlideShare

173035-10-4, 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: conditions 1), NHC.HCl (1.0mmol) was dissolved/suspended in 5mL water. Tollens? reagent was prepared by mixing silver(I) oxide (127mg, 0.548mmol) and concentrated ammonia (0.73mL, 15.3mol/L, 11mmol) until complete dissolution. The reagent was diluted with quantum satis water for a final volume of 5mL. An instantaneous precipitation was observed. After 30minat RT, the white solid was filtered and washed with water. Conditions 2), NHC.HCl (1.0mmol) was dissolved/suspended in 10mL of water or ethanol. Silver(I) oxide (127mg, 0.549mmol) and ammonia (0.65mL, 15.3mol/L, 9.9mmol) were added. After 30-200min at RT, the white solid was isolated by filtration and washed with water (IMes, SIMes) or ethanol (IPr, SIPr).

The synthetic route of 173035-10-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Gibard, Clementine; Fauche, Kevin; Guillot, Regis; Jouffret, Laurent; Traikia, Mounir; Gautier, Arnaud; Cisnetti, Federico; Journal of Organometallic Chemistry; vol. 840; (2017); p. 70 – 74;,
Chiral Catalysts
Chiral catalysts – SlideShare

173035-10-4, 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of SIMes¡¤HCl (906mg, 2.64mmol) in THF (30mL) was added dropwise a 1.6M solution of n-butyl lithium in hexanes (1.65mL, 2.64mmol) at-78C with stirring. After 10min, the suspension was allowed to warm to room temperature for additional 10min. The mixture was cooled again to-78C and then treated with a cooled THF solution (-78C) of mesitylcopper (504mg including 0.09 equivalents of toluene, determined by 1H NMR, 2.64mmol) by means of a cannula. The reaction mixture was allowed to warm to room temperature and stirred for further 18h. The solvents were removed under reduced pressure. The resulting solid residue was dried for 2h and then extracted with toluene (50mL). The suspension was filtered through Kieselgur and the filter cake was washed with small portions of toluene (5mL). The resulting solution was concentrated under reduced pressure to 15mL and then stored at-18C for 18h while large colorless crystals were forming. The mother liquor was decanted from the crystals that were subsequently washed with cold toluene (5mL) and dried in vacuo for 15h. The mother liquor was combined with the washing solution, concentrated to 5mL and stored at-18C for about 3 weeks. From this solution a second crop of colorless crystals was isolated. Combined yield: 1.032g (2.11mmol, 80%). Anal. Calcd for C30H37N2Cu: C, 73.66; H, 7.62; N, 5.73. Found: C, 72.87; H, 7.91; N, 5.72. 1H NMR (500.13MHz, C6D6): delta 2.12 (s, 6H, p-CH3, NHC), 2.15 (s, 6H, o-CH3, CuMes), 2.18 (s, 12H, o-CH3, NHC), 2.26 (s, 3H, p-CH3, CuMes), 3.05 (s, 4H, CH2), 6.76 (s, 4H, CH, NHC), 6.86 (s, 2H, CH, CuMes). 13C NMR (125.77MHz, C6D6): delta 18.1 (o-CH3, NHC), 21.0 (p-CH3, NHC), 21.6 (p-CH3, CuMes), 28.0 (o-CH3, CuMes), 50.4 (CH2), 124.5 (CH, CuMes), 129.6 (CH, NHC), 132.7 (C, CuMes), 136.0, 136.2, 138.2 (3¡ÁC, Mes, NHC), 147.2 (C, CuMes), 163.7 (C, CuMes), 207.1 (C, CN2, NHC). MS (ESI in THF): m/z (rel. intensity)=675 (100) [(NHC)2Cu]+, 857 (34) [(NHC)2Cu2Mes]+; MS (ESI in CH3CN): m/z (rel. intensity)=764 (63) [(NHC)2Cu2(CN)]+, 675 (80) [(NHC)2Cu]+, 410 (42) [(NHC)Cu(CH3CN)]+, 397 (100) [(NHC)Cu(CO)]+, 369 (8) [(NHC)Cu]+, 307 (11) [(Mes)2(C3H4N2)+1]+. IR (KBr, cm-1): 3003, 2949, 2916, 2855, 2729, 2706, 1775, 1742, 1730, 1609, 1589, 1487, 1474, 1439, 1375, 1317, 1306, 1298, 1263, 1215, 1173, 1161, 1032, 1013, 951, 914, 883, 851, 839, 754, 741, 733, 721, 706, 689, 615, 602, 588, 573, 550, 532, 502, 482, 465, 419.

173035-10-4 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride 2734917, achiral-catalyst compound, is more and more widely used in various.

Reference£º
Article; Stollenz, Michael; Fischer, Stefan; Gehring, Henrike; Resch, Stefan G.; Dechert, Sebastian; Grosse, Christian; Meyer, Franc; Journal of Organometallic Chemistry; vol. 821; (2016); p. 106 – 111;,
Chiral Catalysts
Chiral catalysts – SlideShare

173035-10-4, 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A suspension of 383.0 mg (1.08 mmol) of 1,3-bis(2,4,6-trimethylphenyl)-imidazolidinium chloride (commercially available from Aaron Chemistry GmbH, D-85386 Eching) and 0.67 ml (1.14 mmol) of potassium tert.-pentylate (1.7 M in toluene) was suspended in 25 ml hexane and heated at 50 C. for 10 min. A suspension of 500.0 mg (0.54 mmol) of [RuCl2(PCy3)2(3-phenyl-indenylidene)] (commercially available from Umicore AG, D-63457 Hanau-Wolfgang) in 16 ml of hexane was added and the resulting red suspension stirred at 50 C. for 18 h. The reaction mixture was evaporated to dryness and the isolated crude product purified by silica gel chromatography (hexane/diethylether 6:4) to yield 257.0 mg (50%) of the title compound as red crystals. MS: 948.3 (M+). 31P-NMR (121 MHz, C6D6): 25.8 ppm; 1H-NMR (300 MHz, C6D6): 1.00-1.40 (m, 18H); 1.45-1.64 (m, 6H); 1.65-1.95 (m, 6H); 1.80 (s, 3H); 2.23 (s, 6H); 2.38 (s, 3H); 2.85 (s, 3H); 2.87 (s, 3H); 3.10-3.45 (m, 4H); 6.02 (s, 1H); 6.47 (s, 1H); 6.97 (s, 2H); 7.05-7.35 (m, 6H); 7.84 (s, 1H, RuCCH); 7.89 (m, 2H); 9.16 (m, 1H). Anal. calcd. for C54H69N2Cl2PRu: C, 68.34; H, 7.33; N, 2.95. Found: C, 68.61; H, 7.32; N, 2.68.

As the paragraph descriping shows that 173035-10-4 is playing an increasingly important role.

Reference£º
Patent; Puentener, Kurt; Scalone, Michelangelo; US2006/241156; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.173035-10-4,1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride,as a common compound, the synthetic route is as follows.

A suspension of 6.52 g (17.55 mmol) of l,3-bis(2,4,6-trimethylphenyl)-imidazolidinium chloride (commercially available from Umicore AG, D-63457 Hanau- Wolfgang) and 11.40 ml (19.38 mmol) of potassium tert-.pentylate (1.7 M in toluene) in 400 ml of hexane was stirred for 10 min at 500C. After the reaction mixture was evaporated to dryness, the white residue was re- dissolved in 400 ml of hexane and the formed suspension was transferred to a suspension of 4.00 g (5.85 mmol) of [RuCl2(=CH(o-OCH(Me)CO-N-Pyrrolidine)Ph)(PCy3)] in 400 ml of hexane. The resulting reaction mixture was stirred for 23 h at 500C. The formed green suspension was filtered, the filter cake was washed with 60 ml of hexane and dissolved in 50 ml of dichloromethane. 140 ml of water was added, the organic layer was separated, dried over Na2SO4 and evaporated to dryness. The crude product was washed twice with 70 ml of ethyl acetate / pentane 1 :5 and successively with 50 ml of pentane and dried under vacuum at room temperature to yield 2.75 g (66% yield) of the title compound as a green powder.MS: 709.2 (M+). Anal, calcd. for C35H43Cl2N3O2Ru ? 0.9 CH2Cl2: C, 54.80; H, 5.74; N, 5.34, Cl 17.10. Found: C, 54.77; H, 5.76; N, 5.30, Cl 16.30.

173035-10-4 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride 2734917, achiral-catalyst compound, is more and more widely used in various.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/124853; (2009); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.173035-10-4,1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride,as a common compound, the synthetic route is as follows.

General procedure: The appropriate salt 2 (52.44 mmol) was added to a solution of potassium tert-butoxide (6.72 g, 59.93 mmol) in THF (30 mL). Thereaction mixture was stirred at 25 C for 15 min and then filtered.The filtrate was added to a solution of complex 3 (30.00 g,37.46 mmol) in toluene (900 mL). The reaction mixture wasstirred at 80 C for 1.5 h, cooled to 25 C, and filtered. The solvent was removed in vacuo. The red-brown precipitate wassuspended in hexane (500 mL). Then the precipitate was filtered, successively washed with hexane and methanol, and driedin vacuo at 45 C.

As the paragraph descriping shows that 173035-10-4 is playing an increasingly important role.

Reference£º
Article; Shcheglova; Kolesnik; Ashirov; Krasnokutskaya; Russian Chemical Bulletin; vol. 65; 2; (2016); p. 490 – 497; Izv. Akad. Nauk, Ser. Khim.; vol. 65; 2; (2016); p. 490 – 497,8;,
Chiral Catalysts
Chiral catalysts – SlideShare