* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
To a solution of diimine (8.0 g, 27.3 mmol) in THF (100 mL) was added NaBH4 (4.24 g, 112.1 mmol) at 0° C. Concentrated HCl (4.5 mL, 2 eq.) was added dropwise over 30 minutes. After the HCl addition, the reaction mixture was stirred at 0° C. for 20 min. Then, 3 M HCl (250 mL) was added carefully to the flask at 0° C. and the mixture was stirred for an additional 1 hr, allowing the temperature to rise to ambient temperature. The resulting white precipitates were filtered and washed with water (200 mL) and 5percent acetone-ether (150 mL). The product (9.4 g, 93percent) was obtained as a white solid and dried in vacuo. To a suspension of the HCl salt (8.5 g, 23 mmol) in HC(OEt)3 (35 mL, 162 mmol) was added 2 drops of HCO2H (adding about 1 mol percent). The reaction mixture was then heated at 120° C. for 5 hr under Ar. Then, the reaction mixture was cooled to an ambient temperature and hexane (200 mL) was added. The mixture was stirred for 1 hr and the white precipitates were filtered, washed with hexane (200 mL) and dried in vacuo to yield the IMesH2.HCl salt (7.6 g, 96percent).
Reference:
[1] Synlett, 2006, # 3, p. 493 - 495
[2] Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2546 - 2558
[3] Patent: US9403854, 2016, B2, . Location in patent: Page/Page column 41
[4] Tetrahedron, 1999, vol. 55, # 51, p. 14523 - 14534
[5] Organic Syntheses, 2010, vol. 87, p. 77 - 87
[6] Chinese Journal of Chemistry, 2010, vol. 28, # 12, p. 2416 - 2420
[7] Chemistry - A European Journal, 2007, vol. 13, # 25, p. 7195 - 7203
2
[ 64-18-6 ]
[ 258278-23-8 ]
[ 173035-10-4 ]
Yield
Reaction Conditions
Operation in experiment
80%
at 23 - 130℃; Inert atmosphere
A mixture of 1.12 g (3.03 mmol) of N,N'-bis-(2,4,6-trimethylphenylamino)ethane dihydrochloride, 10mL of triethyl orthoformate, and one drop of 96percent formic acid was heated in a distillation apparatus until the ethanol distillation ceased. The temperature of the reaction mixture reached 130 oC. Uponcooling to 23 oC, a colorless solid precipitated which was collected by filtration and dried in vacuo.
Reference:
[1] Journal of Organometallic Chemistry, 2013, vol. 743, p. 44 - 48
3
[ 258278-23-8 ]
[ 173035-10-4 ]
Reference:
[1] Chemical Communications, 2011, vol. 47, # 5, p. 1559 - 1561
With formic acid; at 120℃; for 5h;Inert atmosphere;
To a solution of diimine (8.0 g, 27.3 mmol) in THF (100 mL) was added NaBH4 (4.24 g, 112.1 mmol) at 0 C. Concentrated HCl (4.5 mL, 2 eq.) was added dropwise over 30 minutes. After the HCl addition, the reaction mixture was stirred at 0 C. for 20 min. Then, 3 M HCl (250 mL) was added carefully to the flask at 0 C. and the mixture was stirred for an additional 1 hr, allowing the temperature to rise to ambient temperature. The resulting white precipitates were filtered and washed with water (200 mL) and 5% acetone-ether (150 mL). The product (9.4 g, 93%) was obtained as a white solid and dried in vacuo. To a suspension of the HCl salt (8.5 g, 23 mmol) in HC(OEt)3 (35 mL, 162 mmol) was added 2 drops of HCO2H (adding about 1 mol %). The reaction mixture was then heated at 120 C. for 5 hr under Ar. Then, the reaction mixture was cooled to an ambient temperature and hexane (200 mL) was added. The mixture was stirred for 1 hr and the white precipitates were filtered, washed with hexane (200 mL) and dried in vacuo to yield the IMesH2.HCl salt (7.6 g, 96%).
With orthoformic acid triethyl ester; at 23 - 130℃;Inert atmosphere;
A mixture of 1.12 g (3.03 mmol) of N,N'-bis-(2,4,6-trimethylphenylamino)ethane dihydrochloride, 10mL of triethyl orthoformate, and one drop of 96% formic acid was heated in a distillation apparatus until the ethanol distillation ceased. The temperature of the reaction mixture reached 130 oC. Uponcooling to 23 oC, a colorless solid precipitated which was collected by filtration and dried in vacuo.