Pyridine → Methyl 5-ethylsulfonylamino-2-fluorocarbanilate
Reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=1[F:13].N1C=CC=CC=1>ClCCl>[CH2:18]([S:15]([NH:14][C:9]1[CH:10]=[CH:11][C:12]([F:13])=[C:7]([CH:8]=1)[NH:6][C:2](=[O:3])[O:4][CH3:5])(=[O:17])=[O:16])[CH3:19]Participants
Procedure
22.1 g (229 mmol) of methyl chloroformate was added dropwise to a mixture of 50.0 g (229 mmol) of N-(3-amino-4-fluorophenyl)ethanesulfonamide, 18.1 g (229 mmol) of pyridine and 500 ml of dichloromethane at a temperature of not higher than 5° C. Thereafter the temperature was raised to room temperature and the reaction was continued for 5 hours. After the dichloromethane layer was separated out by adding water to the resultant mixture, the dichloromethane layer was washed with saturated saline solution and dried over anhydrous sodium sulfate. Thereafter the dichloromethane was distilled off to obtain the crude product (crystals). The crude product was washed with diisopropyl ether, thereby obtaining 61.0 g of the objective product (yield: 96%) in the form of light brown crystals.
Workup
- customAfter the dichloromethane layer was separated out
- additionby adding water to the resultant mixture
- washthe dichloromethane layer was washed with saturated saline solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThereafter the dichloromethane was distilled off
- customto obtain the crude product (crystals)
- washThe crude product was washed with diisopropyl ether
Sources & evidence
- ORD record
- ord-d060b7fa82df49f8b9290ad0cf81f7a2
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05416236
Reaction notes
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