Ethyl chloroformate → 1-(N,N-dimethylsulfamoyl)-2-ethoxycarbonyl-5,6-dimethoxybenzimidazole

HRID 476889Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[S:3]([N:6]1[C:10]2[CH:11]=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:9]=2[N:8]=[CH:7]1)(=[O:5])=[O:4].C([Li])CCC.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27]>C1COCC1.CCCCCC>[CH3:19][N:2]([CH3:1])[S:3]([N:6]1[C:10]2[CH:11]=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:9]=2[N:8]=[C:7]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])(=[O:4])=[O:5]

Participants

Conditions

Temperature: -60 °C

Procedure

1-(N,N-dimethylsulfamoyl)-5,6-dimethoxybenzimidazole (5.70 g) was dissolved in dry THF (170 ml) in a dry argon atmosphere, cooled to -60° C. and a solution of n-butyl lithium (1.58M) in hexane (15.2 ml) was added dropwise and stirred for 30 minutes. After ethyl chloroformate (2.60 g) was added dropwise, the mixture was slowly returned to room temperature and allowed to react overnight. THF was distilled off, the residue was dissolved in ethyl acetate, washed with water and dried over anhydrous Na2SO4, and the solvent was distilled off. Purification of the residue by column chromatography on silica gel gave the title compound (5.13 g) as an oily product.

Workup

customwas slowly returned to room temperature
customto react overnight
distillationTHF was distilled off
dissolutionthe residue was dissolved in ethyl acetate
washwashed with water
dry with materialdried over anhydrous Na2SO4
distillationthe solvent was distilled off
customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record: ord-4b9b11e49fc342c79e678a2f60b26fa9
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886803

Reaction notes

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