Pyridine → HCID 53972694, compound

HRID 248750

Reaction equation

HRID 248750 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.N1C=CC=CC=1.[CH3:19][O:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:19][O:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](=[O:29])(=[O:30])[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

5

Reactant 3

HCID 1049PyridineHCID 678534-Fluoro-2-(trifluoromethyl)anilineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

Product 1

HCID 53972694HCID 53972694, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 ml of dichloromethane is combined with 9.38 g (52.37 mmol) of 4-fluoro-2-trifluoromethylaniline and 6 ml (14.3 mmol) of pyridine. The mixture is cooled with ice water and under agitation and exclusion of moisture, 13.52 g (57.62 mmol) of 2-chlorosulfonylbenzoic acid methyl ester is added in small increments. The mixture is agitated overnight, washed with 2N hydrochloric acid and water, the dichloromethane solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized from ethyl acetate/hexane. The title compound melts at 143°-145° C.

Workup

  1. additionis added in small increments
  2. washwashed with 2N hydrochloric acid and water
  3. dry with materialthe dichloromethane solution is dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a6fedd8e9f7a413da2a41d0ee8a8f102
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Linked notes

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