Azobisisobutyronitrile → Ethyl 4-[4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]butanoate
Reaction equation
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13](=[O:15])[NH:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].N(C(C)(C)C#N)=NC(C)(C)C#N.[Cl:36]N1C(=O)CCC1=O>ClC1C=CC=CC=1>[Cl:36][C:9]1[C:10]2[NH:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]=2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=1Participants
5
Conditions
- Temperature
- 85 °C
Procedure
To a solution of ethyl 4-[7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]butanoate (9.7 g, 30.5 mmol) and 2,2′-azobisisobutyronitrile (AIBN; 0.5 g, 3.05 mmol) in chlorobenzene (100 mL) was added N-chlorosuccinimide (NCS; 4.35 g, 32.6 mmol) in portions at 65° C., and the mixture was stirred at 80-90° C. for 2 days. After cooled to room temperature, the reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous phase was extracted with ethyl acetate (100 ml×3), washed with brine (100 mL), dried over anhydrous sodium sulfate and purified by silica gel column (petroleum ether/ethyl acetate, 50/1) to afford the title compound (6.8 g, 61%) as yellow oil.
Workup
- temperatureAfter cooled to room temperature
- customthe reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
- extractionThe aqueous phase was extracted with ethyl acetate (100 ml×3)
- washwashed with brine (100 mL)
- dry with materialdried over anhydrous sodium sulfate
- custompurified by silica gel column (petroleum ether/ethyl acetate, 50/1)
Sources & evidence
- ORD record
- ord-f2c459bfef284caea5d495ca1d86a039
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785460B2
Reaction notes
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