Acetyl chloride → Methyl 4-acetamido-2,5-dimethylbenzoate
Reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[C:19]([CH3:20])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:21])[CH:11]=1.[C:22](Cl)(=[O:24])[CH3:23].C(=O)([O-])O.[Na+]>ClCCl>[C:22]([NH:9][C:10]1[C:19]([CH3:20])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:21])[CH:11]=1)(=[O:24])[CH3:23]Participants
Procedure
Triethylamine (1.16 ml, 8.32 mmol) was added to a suspension of methyl 4-amino-2,5-dimethylbenzoate monohydrochloride (0.600 g, 2.78 mmol) in dichloromethane (8 ml), and the resulting mixture was cooled with ice water, followed by adding dropwise thereto a solution of acetyl chloride (0.263 g, 3.35 mmol) in dichloromethane (2 ml). The resulting mixture was heated to room temperature and stirred for 3 hours, and then acetyl chloride (0.262 g, 3.34 mmol) was further added thereto and stirred for 1.5 hours. The resulting mixture was added to a saturated aqueous sodium hydrogencarbonate solution and extracted three times with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain methyl 4-(acetylamino)-2,5-dimethylbenzoate (0.685 g, 99%).
Workup
- additionby adding dropwise
- stirringstirred for 1.5 hours
- extractionextracted three times with ethyl acetate
- washthe organic layer was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-6d0f561250cb440391fdfb37f13e2f06
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199147B2
Reaction notes
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