Acetic Anhydride → 2-Acetylamino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15].[C:17](OC(=O)C)(=[O:19])[CH3:18].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([C:11]([F:13])([F:14])[F:12])=[CH:6][C:5]=1[NH:15][C:17](=[O:19])[CH3:18]Participants
Procedure
A solution of 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (42.0 g, 122 mmol) in toluene (400 mL) was treated with acetic anhydride (12.8 mL, 135 mmol) and the mixture was heated to reflux for 16 h under nitrogen. It was then allowed to cool to r.t. and diluted with water. The mixture was rendered neutral by adding small portions of sodium hydrogencarbonate, and the organic layer was separated. The aqueous phase was extracted with EtOAc, and the combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was recrystallized in hexanes to give 2-acetylamino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (43.4 g, 112 mmol, 92%) as a white powder, m.p. 96-98° C., ESI-MS: m/z 388 [M+H]+.
Workup
- temperaturethe mixture was heated
- temperatureto reflux for 16 h under nitrogen
- customthe organic layer was separated
- extractionThe aqueous phase was extracted with EtOAc
- dry with materialthe combined organic phases were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was recrystallized in hexanes
Sources & evidence
- ORD record
- ord-0732c87d09654ddba4e8745bcffb6952
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07655666B2
Reaction notes
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