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[ CAS No. 250285-32-6 ]

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Chemical Structure| 250285-32-6
Chemical Structure| 250285-32-6
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CAS No. :250285-32-6 MDL No. :MFCD02684545
Formula : C27H37ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :425.05 g/mol Pubchem ID :2734913
Synonyms :

Safety of [ 250285-32-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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  • Upstream synthesis route of [ 250285-32-6 ]
  • Downstream synthetic route of [ 250285-32-6 ]

[ 250285-32-6 ] Synthesis Path-Upstream   1~20

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YieldReaction ConditionsOperation in experiment
70% With hydrogenchloride In 1,4-dioxane; ethyl acetate at 0 - 20℃; for 2 h; Charging a 1000 mL round bottom flask with methanol (500 mL), 2,6-diisopropylaniline (63.8 mL, 340 mmol), glyoxal (40 wt percent soln in water, 19 mL, 170 mmol), and formic acid (1 mL).Stirring the resulting mixture for 3 hours at room temperature.Filtering the yellow precipitate, (3) (Diagram D)Washing precipitate with cold methanol.Drying precipitate in vacuo overnight (70percent, 44.2 g, 238 mmol).Charging a 5 L round bottom flask with precipitate (3) (200 g, 532 mmol) and ethyl acetate (2 L).Stirring the resulting mixture until (3) was dissolved.Cooling the solution to 0° C. but this can be carried out at room temperature.Charging a 500 mL Erlenmeyer flask with paraformaldehyde (20.7 g, 690 mmol), HCl (4N in dioxane, 212 mL, 851 mmol).Stirring this solution for 10 minutes, then added.Stirring the resulting mixture for 2 hours at room temperature.Filtering precipitateDissolving precipitate in methanol (200 mL).Adding 15.0 g of sodium bicarbonate.Stirring the solution for 1 hour or until there is no more carbonation.Filtering the solution to remove the solids.Reprecipitating the product with 250 mL of diethyl etherCollecting product by filtrationWashing product with diethyl ether.Drying the product in vacuo to yield IPr.HCl (4) as a white powder (70percent, 158.25 g, 371 mmol). 1H NMR (CDCl3, 400 MHz) δ 10.1 (s, 1H), 8.15 (s, 2H), 7.57 (t, 2H, J=7.8 Hz), 7.35 (d, 4H, J=8.4 Hz), 2.43(m, 4H), 1.28 (m, 24H) 13C NMR (CDCl3, 400 MHz) δ 145, 132.1, 129.9, 126.8, 124.7, 29.1, 24.7, 23.7. Synthesis of 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride (IPr.HCl, 4)A 1000 mL round bottom flask was charged with methanol (500 mL), 2,6-diisopropylaniline (63.8 mL, 340 mmol), glyoxal (40 wt percent soln in water, 19 mL, 170 mmol), and formic acid (1 mL). The resulting mixture was allowed to stir for 3 hours at room temperature. The yellow precipitate (3) was filtered, washed with cold methanol and dried in vacuo overnight (70percent, 44.2 g, 238 mmol). A 5 L round bottom flask was charged with 3 (200 g, 532 mmol) and ethyl acetate (2 L) and the resulting mixture was stirred until 3 was dissolved. The solution was cooled to 0° C. A 500 mL Erlenmeyer flask was charged with paraformaldehyde (20.7 g, 690 mmol), HCl (4N in dioxane, 212 mL, 851 mmol). This solution was stirred for 10 minutes, then added. The resulting mixture was then stirred for 2 hours at room temperature. The precipitate was filtered, dissolved in methanol (200 mL) and 15.0 g of sodium bicarbonate was added. The solution was stirred for 1 hour or until there was no more carbonation. The solution was filtered to remove the solids and the product was reprecipitated with 250 mL of diethyl ether, collected by filtration, washed with diethyl ether and dried in vacuo to yield IPr.HCl (4) as a white powder (70percent, 158.25 g, 371 mmol). 1H NMR (CDCl3, 400 MHz) δ 10.1 (s, 1H), 8.15 (s, 2H), 7.57 (t, 2H, J=7.8 Hz), 7.35 (d, 4H, J=8.4 Hz), 2.43(m, 4H), 1.28 (m, 24H) 13C NMR (CDCl3, 400 MHz) δ 145, 132.1, 129.9, 126.8, 124.7, 29.1, 24.7, 23.7.
70% With hydrogenchloride In 1,4-dioxane; ethyl acetate at 0 - 20℃; for 2 h; Synthesizing of l,3-Bis(2,6-dsopropylphenyl)imidazolium chloride (IPr HCl, 4) by:; Charging a 1000 mL round bottom flask with methanol (500 mL), 2,6- diisopropylaniline (63.8 mL, 340 mmol), glyoxal (40wt percent soln in water, 19 mL, 170 mmol), and formic acid (ImL).Stirring the resulting mixture for 3 hours at room temperature. Filtering the yellow precipitate, (3) (Diagram D)Washing precipitate with cold methanol.Drying precipitate in vacuo overnight (70percent, 44.2 g, 238 mmol).Charging a 5 L round bottom flask with precipitate (3) (200 g, 532 mmol) and ethyl acetate (2 L). Stirring the resulting mixture until (3) was dissolved.Cooling the solution to 0° C but this can be carried out at room temperature.Charging a 500 mL Erlenmeyer flask with paraformaldehyde (20.7 g, 690 mmol), HCl (4N in dioxane, 212 mL, 851 mmol).Stirring this solution for 10 minutes, then added. Stirring the resulting mixture for 2 hours at room temperature.Filtering precipitateDissolving precipitate in methanol (20OmL).Adding 15.Og of sodium bicarbonate.Stirring the solution for 1 hour or until there is no more carbonation. Filtering the solution to remove the solids.Reprecipitating the product with 250 mL of diethyl etherCollecting product by filtrationWashing product with diethyl ether.Drying the product in vacuo to yield IPrHCl (4) as a white powder (70percent, 158.25g, 371 mmol). 1H NMR (CDCl3, 400 MHz) δ 10.1 (s, IH), 8.15 (s, 2H), 7.57 (t,2H, J = 7.8 Hz), 7.35 (d, 4H, J = 8.4 Hz), 2.43(m, 4H), 1.28 (m, 24H) 13C NMR (CDCl3, 400 MHz) δ 145, 132.1, 129.9, 126.8, 124.7, 29.1, 24.7, 23.7.; Synthesis of l,3-Bis(2,6-diisopropyIphenyl)imidazolium chloride (IPrηCl, 4); A l 000 mL round bottom flask was charged with methanol (500 mL), 2,6- diisopropylamline (63.8 mL, 340 mmol), glyoxal (40wt percent soln in water, 19 mL, 170 mmol), and formic acid (ImL). The resulting mixture was allowed to stir for 3 hours at room temperature. The yellow precipitate (3) was filtered, washed with cold methanol and dried in vacuo overnight (70percent, 44.2 g, 238 mmol). A 5 L round bottom flask was charged with 3 (200 g, 532 mmol) and ethyl acetate (2 L) and the resulting mixture was stirred until 3 was dissolved. The solution was cooled to 0° C. A 500 mL Erlenmeyer flask was charged with paraformaldehyde (20.7 g, 690 mmol), HCl (4N in dioxane, 212 mL, 851 mmol). This solution was stirred for 10 minutes, then added. The resulting mixture was then stirred for 2 hours at room temperature. The precipitate was filtered, dissolved in methanol (20OmL) and 15.Og of sodium bicarbonate was added. The solution was stirred for 1 hour or until there was no more carbonation. The solution was filtered to remove the solids and the product was reprecipitated with 250 mL of diethyl ether, collected by filtration, washed with <n="10"/>diethyl ether and dried in vacuo to yield IPrHCl (4) as a white powder (70percent, 158.25g, 371 mmol). 1H NMR (CDCl3, 400 MHz) δ 10.1 (s, IH), 8.15 (s, 2H), 7.57 (t, 2H, J = 7.8 Hz), 7.35 (d, 4H, J = 8.4 Hz), 2.43(m, 4H), 1.28 (m, 24H) 13C NMR (CDCl3, 400 MHz) δ 145, 132.1, 129.9, 126.8, 124.7, 29.1, 24.7, 23.7.
51.7%
Stage #1: With hydrogenchloride In toluene at 50℃; for 1 h;
Stage #2: With hydrogenchloride In 1,4-dioxane at 40℃; for 40 h;
37.6 g (100 mmol) of bis(2,6-diisopropylphenyl)diazabutadiene, 1.68 g (100 mmol) of formaldehyde solid, 160 mL of toluene were added to a 500 mL three-neck round bottom flask. Stirred refluxed at 50° C. for 1 h until most of the formaldehyde dissolved. The reaction mixture was cooled to 40° C. and a solution of HCl in dioxane 58 mL (100 mmol, 1.723 mol/L) was added with a syringe.The color of the solution changed from yellow to red to brown, with the development of a white solid. The reaction was stirred and refluxed at 40° C. for 40 h, suction filtered and washed three times with THF to give a pink solid mass. About 40 mL of anhydrous ethanol was added to dissolve, the solvent was derotated, the solid was turned into a powder, and washed three times with THF to obtain 21.94 g of an off-white powder HIPrCl (yield 51.7percent).
Reference: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 4, p. 622 - 630
[2] Journal of the American Chemical Society, 2011, vol. 133, # 30, p. 11482 - 11484
[3] Inorganic Chemistry, 2017, vol. 56, # 8, p. 4568 - 4575
[4] Organic Process Research and Development, 2014, vol. 18, # 8, p. 1041 - 1044
[5] Patent: US7109348, 2006, B1, . Location in patent: Page/Page column 4-7
[6] Patent: WO2008/36084, 2008, A1, . Location in patent: Page/Page column 4; 6-7; 8-9
[7] European Journal of Organic Chemistry, 2012, # 31, p. 6218 - 6227
[8] Patent: CN106432307, 2017, A, . Location in patent: Paragraph 0031; 0032
[9] Journal of Organometallic Chemistry, 2007, vol. 692, # 24, p. 5390 - 5394
[10] Green Chemistry, 2018, vol. 20, # 5, p. 964 - 968
[11] ChemCatChem, 2018, vol. 10, # 11, p. 2450 - 2457
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Reference: [1] Chemical Communications, 2011, vol. 47, # 5, p. 1559 - 1561
[2] Tetrahedron, 1999, vol. 55, # 51, p. 14523 - 14534
[3] Journal of Organic Chemistry, 2008, vol. 73, # 7, p. 2784 - 2791
[4] Journal of the American Chemical Society, 2008, vol. 130, # 31, p. 10082 - 10083
[5] Advanced Synthesis and Catalysis, 2014, vol. 356, # 11-12, p. 2539 - 2546
[6] Tetrahedron, 2012, vol. 68, # 38, p. 7949 - 7955
[7] Journal of Organometallic Chemistry, 2016, vol. 825-826, p. 55 - 62
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Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, p. 5683 - 5686[2] Angewandte Chemie, 2009, vol. 121, p. 5793 - 5796
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 17, p. 4668 - 4672[2] Angew. Chem., 2018, vol. 130, # 17, p. 4758 - 4762,5
[3] Journal of Organometallic Chemistry, 2000, vol. 606, # 1, p. 49 - 54
[4] Organic Letters, 2016, vol. 18, # 3, p. 432 - 435
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Reference: [1] Organic Letters, 2015, vol. 17, # 3, p. 544 - 547
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Reference: [1] Journal of Organometallic Chemistry, 2000, vol. 606, # 1, p. 49 - 54
[2] Tetrahedron, 1999, vol. 55, # 51, p. 14523 - 14534
[3] Tetrahedron, 2012, vol. 68, # 38, p. 7949 - 7955
[4] Advanced Synthesis and Catalysis, 2014, vol. 356, # 11-12, p. 2539 - 2546
[5] Organic Process Research and Development, 2014, vol. 18, # 8, p. 1041 - 1044
[6] Organic Letters, 2015, vol. 17, # 3, p. 544 - 547
[7] Advanced Synthesis and Catalysis, 2016, vol. 358, # 4, p. 622 - 630
[8] Journal of Organometallic Chemistry, 2016, vol. 825-826, p. 55 - 62
[9] Dalton Transactions, 2016, vol. 45, # 44, p. 17859 - 17866
[10] Inorganic Chemistry, 2017, vol. 56, # 8, p. 4568 - 4575
[11] Patent: CN106432307, 2017, A,
[12] Angewandte Chemie - International Edition, 2018, vol. 57, # 17, p. 4668 - 4672[13] Angew. Chem., 2018, vol. 130, # 17, p. 4758 - 4762,5
[14] ChemCatChem, 2018, vol. 10, # 11, p. 2450 - 2457
[15] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11339 - 11343[16] Angew. Chem., 2018, vol. 130, # 35, p. 11509 - 11513,5
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Reference: [1] Dalton Transactions, 2016, vol. 45, # 44, p. 17859 - 17866
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Reference: [1] Applied Organometallic Chemistry, 2013, vol. 27, # 10, p. 578 - 587
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Reference: [1] Organometallics, 2018, vol. 37, # 9, p. 1483 - 1492
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11339 - 11343[2] Angew. Chem., 2018, vol. 130, # 35, p. 11509 - 11513,5
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Reference: [1] Organometallics, 2017, vol. 36, # 10, p. 1981 - 1992
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Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 52, p. 14204 - 14208[2] Angew. Chem., 2013, vol. 125, # 52, p. 14454 - 14458,5
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Reference: [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 16, p. 2929 - 2932
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YieldReaction ConditionsOperation in experiment
94% With sodium t-butanolate In tetrahydrofuran at 20℃; for 20 h; Synthesis of [(IPr)CuCl]. This synthesis is as reported in the literature; see H. Kaur et al., Organometallics 2004, 23, 1157-1160. In a 250 mL Schlenk flask were added copper(I) chloride (1.0 g, 10.10 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr.HCl; 4.29 g, 10.10 mmol), and sodium tert-butoxide (0.97 g, 10.10 mmol). To this flask, dry tetrahydrofuran (100 mL) was added under an inert atmosphere of argon, and the mixture was magnetically stirred for 20 hours at room temperature. After the mixture was filtered through a plug of Celite and then evaporating the solvent under vacuum, a white solid was obtained (4.59 g, 9.40 mmol, 94percent). 1H NMR: (400 MHz, acetone-d6, ppm) δ=1.21 (d, J=6.8 Hz, 12H); 1.30 (d, J=6.8 Hz, 12H); 2.57 (hep, J=6.8 Hz, 4H); 7.12 (s, 2H). 7.29 (d, J=7.8 Hz, 4H); 7.49 (t, J=7.8 Hz, 2H). 13C NMR: (100 MHz, acetone-d6, ppm) δ=182.32; 145.61; 134.41; 130.62; 124.25; 123.13; 28.76; 24.82; 23.87. Elemental analysis calcd for C27H36ClCuN2: C 66.64percent, H, 7.46percent, N, 5.76percent; found C, 66.70percent, H, 7.48percent, N, 6.06percent.
Reference: [1] Organometallics, 2004, vol. 23, # 5, p. 1157 - 1160
[2] Patent: US2009/69569, 2009, A1, . Location in patent: Page/Page column 6
[3] Organometallics, 2013, vol. 32, # 15, p. 4279 - 4283
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 47, p. 9334 - 9337
[5] Journal of the American Chemical Society, 2017, vol. 139, # 36, p. 12855 - 12862
[6] Journal of the American Chemical Society, 2015, vol. 137, # 4, p. 1424 - 1427
[7] Dalton Transactions, 2017, vol. 46, # 27, p. 8756 - 8762
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YieldReaction ConditionsOperation in experiment
40% at 80 - 90℃; for 30 h; Add ligand L8850mg (2.0mmol), copper powder 128mg (2.0mmol) in 50mL flask, water 30 mL, 80 ~ 90 in an oil bath, the reaction was stirred for 30 hours, the reaction mixture was cooled to room temperature, filtered, the filter cake was washed 3 times with water, the filter cake dissolved in acetonitrile and filtered to remove unreacted copper powder, the solvent was evaporated under reduced pressure to give 390 mg of colorless crystals, a yield of 40percent.
Reference: [1] Dalton Transactions, 2015, vol. 44, # 4, p. 1836 - 1844
[2] Chemical Science, 2017, vol. 8, # 2, p. 1086 - 1089
[3] Chemical Communications, 2012, vol. 48, # 40, p. 4887 - 4889
[4] Patent: CN105585584, 2016, A, . Location in patent: Paragraph 0046; 0047; 0048
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Reference: [1] Dalton Transactions, 2010, vol. 39, # 19, p. 4489 - 4491
[2] Organic Letters, 2013, vol. 15, # 5, p. 996 - 999
[3] Inorganic Chemistry, 2014, vol. 53, # 17, p. 9181 - 9191
[4] Organometallics, 2010, vol. 29, # 7, p. 1518 - 1521
[5] RSC Advances, 2017, vol. 7, # 9, p. 4912 - 4920
[6] RSC Advances, 2016, vol. 6, # 85, p. 82401 - 82408
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Reference: [1] Organometallics, 2013, vol. 32, # 23, p. 7225 - 7233
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Reference: [1] Inorganic Chemistry, 2009, vol. 48, # 14, p. 6353 - 6355
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Reference: [1] Heteroatom Chemistry, 2012, vol. 23, # 6, p. 605 - 609
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Reference: [1] Heteroatom Chemistry, 2012, vol. 23, # 6, p. 605 - 609
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