Water → 2-chloro-N-methoxybenzenesulfonamide

HRID 1356686

Reaction equation

HRID 1356686 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12](Cl)(=[O:14])=[O:13].O>N1C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:4][O:2][CH3:3])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 761872-Chlorobenzenesulfonyl chlorideHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 185093192-chloro-N-methoxybenzenesulfonamideYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxylamine hydrochloride (0.95 g (11.4 mmol)) was suspended in pyridine (4.0 ml). To this, under cooling with ice and with stirring, 2-chlorobenzenesulfonyl chloride (2.11 g (10.0 mmol)) was added and the mixture was stirred under cooling with ice for one hour and at room temperature for one hour. Water (50.0 ml) was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, dilute hydrochloric acid and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.41 g (64%) of 2-chloro-N-methoxybenzenesulfonamide as pale yellow crystals.

Workup

  1. temperatureTo this, under cooling with ice
  2. stirringthe mixture was stirred
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with water, dilute hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4efb0fd2c384e50846b9f1491dd9f57
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Linked notes

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