Reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:17]([OH:19])=[O:18].[CH3:20]O>>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:12]=2)[S:4][C:3]=1[C:17]([O:19][CH3:20])=[O:18]Participants
3
Conditions
- Temperature
- 30 °C
Procedure
A mixture of 3-methyl-5[4-(trifluoromethyl)phenyl]thiophene-2-carboxylic acid (intermediate 130, 8.1 g) in methanol (300 ml) was heated at 30° C. and hydrogen chloride gas bubbled through the mixture. The reaction mixture was then stirred at reflux for 21 hours; cooled and treated with further hydrogen chloride gas. The reaction mixture was stirred at reflux for a further 6 hours, cooled and concentrated. The resulting precipitate was filtered and washed with cyclohexane to give the title compound as a solid.
Workup
- customhydrogen chloride gas bubbled through the mixture
- temperatureat reflux for 21 hours
- temperaturecooled
- additiontreated with further hydrogen chloride gas
- stirringThe reaction mixture was stirred
- temperatureat reflux for a further 6 hours
- temperaturecooled
- concentrationconcentrated
- filtrationThe resulting precipitate was filtered
- washwashed with cyclohexane
Sources & evidence
- ORD record
- ord-39764b49df2e448c85ecf3cdf691af3a
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091237B2
Linked notes
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