Acetyl chloride → Methyl 3-(acetylamino)-2-iodobenzoate
Reaction equation
[NH2:1][C:2]1[C:3]([I:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>C(Cl)Cl.O>[C:20]([NH:1][C:2]1[C:3]([I:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:22])[CH3:21]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 3-amino-2-iodobenzoate (70.0 g, 253 mmol) in methylene chloride (1000 mL) was added triethylamine (52.8 mL, 379 mmol) and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added acetyl chloride (35.9 mL, 505 mmol) at 0° C. and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/10) to give the title compound (76.6 g, yield 95%).
Workup
- stirringthe mixture was stirred at room temperature for 4 hr
- extractionextracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/10)
Sources & evidence
- ORD record
- ord-66e6ae64cc92405ea571b48c6759a00d
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110585B2
Reaction notes
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