Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8][C:7]=1[NH2:15])=[O:5])[CH3:2].N1C=CC=CC=1.CO[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1OC)[C:27](Cl)=[O:28].[CH2:35]([Cl:37])Cl>>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8][C:7]=1[NH:15][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[C:24]([CH2:35][Cl:37])[CH:25]=1)=[O:5])[CH3:2]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
2-Amino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester (Compound A) (4.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (2.8 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (3.0 ml) were added at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added, and the mixture was subjected to separatory extraction with chloroform, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-(3-chloromethyl-benzoylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester as a useful intermediate (7.42 g, yield 100%).
Workup
- customAfter the completion of the reaction
- distillationdistilled water
- additionwas added
- extractionthe mixture was subjected to separatory extraction with chloroform
- washthe organic layer was washed with saturated brine
- dry with materialwas dried over sodium sulfate
- concentrationwas then concentrated
Sources & evidence
- ORD record
- ord-d039a63894f94c38830b00a29956f7a9
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08134015B2
Linked notes
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