Hydrochloric Acid → 2-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-acetic acid methyl ester

HRID 654010

Reaction equation

[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[CH3:13][O:14][C:15](=[O:21])[CH2:16][S:17](Cl)(=[O:19])=[O:18].Cl>N1C=CC=CC=1.ClCCl>[CH3:13][O:14][C:15](=[O:21])[CH2:16][S:17](=[O:19])(=[O:18])[NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=1[C:9]([F:10])([F:11])[F:12]

Participants

Conditions

Temperature: 0 °C

Procedure

5 g (27.64 mmol) of 4-fluoro-2-(trifluoromethyl)-aniline is dissolved in 25 ml of dry pyridine and the solution is cooled to 0° C. A solution of 4.82 g (27.4 mmol) of chlorosulfonyl acetic acid methyl ester in 20 ml of dichloromethane is instilled in the cooled solution in the course of about 10 minutes with the temperature being maintained. Then it is stirred for 6 hours at room temperature. The reaction solution is then diluted with 100 ml of dichloromethane, the pyridine is shaken out with 2N hydrochloric acid, the organic phase is dried on magnesium sulfate, filtered and evaporated to dryness. The residue is crystallized from diethyl ether/hexane yield is obtained as a crystallizate. Melting point 84°-86° C.

Workup

customis instilled in the cooled solution in the course of about 10 minutes with the temperature
temperaturebeing maintained
customthe organic phase is dried on magnesium sulfate
filtrationfiltered
customevaporated to dryness
customThe residue is crystallized from diethyl ether/hexane
customyield
customis obtained as a crystallizate

Sources & evidence

ORD record: ord-a33c0f384d364543b7c03887fdc98fb1
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130119

Linked notes

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