Chlorosuccinimide → Isopropyl [4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

HRID 1698572Notes

Reaction equation

[CH:1]([O:4][C:5](=[O:22])[CH2:6][N:7]1[C:11]2[C:12]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8]1=[O:21])([CH3:3])[CH3:2].[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(=O)([O-])O.[Na+].N(C(C)(C)C#N)=NC(C)(C)C#N>[CH:1]([O:4][C:5](=[O:22])[CH2:6][N:7]1[C:11]2[C:12]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:13][CH:14]=[C:15]([Cl:23])[C:10]=2[NH:9][C:8]1=[O:21])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of isopropyl[7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate (5.29 g, 17.4 mmol) in carbon tetrachloride (350 mL) was added N-chlorosuccinimide (2.55 g, 19.1 mmol) and 2,2′-azobisisobutyronitrile (86 mg, 0.522 mmol), and the mixture was stirred at 70° C. for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with dichloromethane (X2). The combined organic layer was washed with water (X1) and brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 10-50% ethyl acetate/hexane gradient mixture to give 3.83 g (11.3 mmol, 65.0%) of the title compound as a colorless solid.

Workup

extractionextracted with dichloromethane (X2)
washThe combined organic layer was washed with water (X1) and brine (X1)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography
washeluting with a 10-50% ethyl acetate/hexane gradient mixture

Sources & evidence

ORD record: ord-5c11c799a533448cbc62c47839faa704
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163935B2

Reaction notes

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