Pyridine → 2-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic Acid Methyl Ester

HRID 248753Notes

Reaction equation

[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].N1C=CC=CC=1.[CH3:19][O:20][C:21](=[O:27])[CH2:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:19][O:20][C:21](=[O:27])[CH2:22][S:23](=[O:25])(=[O:24])[NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([C:9]([F:10])([F:11])[F:12])[CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

13.02 g (72.70 mmol) of 4-fluoro-3-trifluoromethylaniline and 6.79 ml (84.12 mmol) of pyridine are dissolved in 350 ml of dichloromethane. The mixture is cooled to 0° C. and then, under agitation and exclusion of moisture, 13.2 g (72.70 mmol) of 2-chlorosulfonylacetic acid methyl ester (95.3%), dissolved in 50 ml of dichloromethane, is added dropwise thereto. After agitation overnight, the mixture is washed with 2N hydrochloric acid and water. The dichloromethane solution is dried over sodium sulfate, concentrated to dryness under vacuum, and the residue is crystallized from diethyl ether/hexane. The title compound melts at 111-°113° C.

Workup

additionis added dropwise
washthe mixture is washed with 2N hydrochloric acid and water
dry with materialThe dichloromethane solution is dried over sodium sulfate
concentrationconcentrated to dryness under vacuum
customthe residue is crystallized from diethyl ether/hexane
customat 111-°113° C.

Sources & evidence

ORD record: ord-9db925dc5e6740fc9854f9cb2cebb278
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05210290

Reaction notes

Loading…