Hydrochloric Acid → Ethyl [7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate
Reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:10]2[C:11]([CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:12][CH:13]=[CH:14][C:9]=2[N:8](C(OC(C)(C)C)=O)[C:7]1=[O:27])[CH3:2].Cl>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:16]([CH:15]([C:11]1[C:10]2[N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:28])[C:7](=[O:27])[NH:8][C:9]=2[CH:14]=[CH:13][CH:12]=1)[CH2:18][CH3:19])[CH3:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of tert-butyl 3-(2-ethoxy-2-oxoethyl)-4-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate (6.16 g, 15.8 mmol) in ethyl acetate (15 mL) was added a 4N solution of hydrogen chloride in ethyl acetate (15 mL) at 0° C., and the mixture was stirred at the same temperature for 2 hr. An additional 4N solution of hydrogen chloride in ethyl acetate (15 mL) was added to the mixture at 0° C., followed by stirring at the same temperature for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting solid was washed with n-hexane to give the title compound (4.28 g, 14.7 mmol, 93%) as a colorless crystal.
Workup
- stirringby stirring at the same temperature for 1 hr
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- washThe resulting solid was washed with n-hexane
Sources & evidence
- ORD record
- ord-25a523de718241ab9ff33dee61f8ddf6
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785460B2
Reaction notes
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