Methanesulfonyl chloride → Methyl 4-fluoro-2-[(methylsulfonyl)amino]benzoate

HRID 2371447Notes

Reaction equation

HRID 2371447 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:8]=[C:9]([NH2:17])[C:10](=[CH:15][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12]>N1C=CC=CC=1>[CH3:1][S:2]([NH:17][C:9]1[C:10](=[CH:15][CH:16]=[C:7]([F:6])[CH:8]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 14075433Methyl 2-amino-4-fluorobenzoate

Product 1

HCID 19907320Methyl 4-fluoro-2-[(methylsulfonyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.68 g) was added dropwise to a stirred solution of methyl 4-fluoroanthranilate (1 g) in pyridine (dried over 4A sieves, 10 ml) at 0°-5°. After 18 hours at room temperature, the mixture was cooled to 0°-5° and further methanesulphonyl chloride (0.68 g) was added dropwise. The mixture was stirred for 24 hours at room temperature. Aqueous work up and recrystallisation from ethanol gave methyl N-(methylsulphonyl)-4-fluoroanthranilate, mp 115.5°-116.5°. (Compound 19).

Workup

  1. temperaturethe mixture was cooled to 0°-5°
  2. customAqueous work up and recrystallisation from ethanol

Sources & evidence

ORD record
ord-40092b39ad284d2b9d73d56d0d676ffc
Source dataset
uspto-grants-1992_03
Patent number
US05093364

Reaction notes

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