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

HRID 654047Notes

Reaction equation

HRID 654047 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].[CH3:13][O:14][C:15](=[O:21])[CH2:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1.ClC(Cl)C>[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])=[C:3]([C:9]([F:10])([F:11])[F:12])[CH:4]=1

Participants

5

Reactant 2

HCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 11435213Methyl (chlorosulfonyl)acetate

Product 1

HCID 542944922-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Analogously to the instructions for example 7, 5 g (27.64 mmol) of 4-fluoro-3-(trifluoromethyl)-aniline in 25 ml of dry pyridine is reacted with 4.82 g (27.4 mmol) of chlorosulfonyl acetic acid methyl ester in 100 ml of dry dichloroethane. After crystallization from ether/hexane, 7.35 g=84.35% of the theoretical yield is obtained. Melting point 111°-112° C.

Workup

  1. customAfter crystallization from ether/hexane, 7.35 g=84.35% of the
  2. customtheoretical yield
  3. customis obtained

Sources & evidence

ORD record
ord-e66a9e9d905045f39c9a250f1f72d803
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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