Hydrochloric Acid → HCID 54423814, compound

HRID 248748

Reaction equation

HRID 248748 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:22])[CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19].ClC(Cl)C.Cl>N1C=CC=CC=1>[CH3:13][O:14][C:15](=[O:22])[CH2:16][CH2:17][S:18](=[O:20])(=[O:19])[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 678534-Fluoro-2-(trifluoromethyl)anilineHCID 4962888Methyl 3-(chlorosulfonyl)propanoate

Product 1

HCID 54423814HCID 54423814, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

8.96 g (50 mmol) of 4-fluoro-2-trifluoromethylaniline is dissolved in 100 ml of pyridine and under cold conditions combined under stirring with 9.52 g (50 mmol) of 3-chlorosulfonylpropionic acid methyl ester (98.5%). The mixture is agitated for 20 minutes, heated for 4 hours to 40° C., and the pyridine is exhausted under vacuum. The residue is distributed between dichloroethane and 4N hydrochloric acid. The organic solution is washed with water, dried over sodium sulfate, and concentrated to dryness under vacuum. The residue is purified by column chromatrography on silica gel. The title compound is eluted with ethyl acetate.

Workup

  1. temperatureheated for 4 hours to 40° C.
  2. washThe organic solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is purified by column chromatrography on silica gel
  6. washThe title compound is eluted with ethyl acetate

Sources & evidence

ORD record
ord-d18b19c5760f4c7a9fe769c7ee4fafca
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Linked notes

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