3-(Trifluoromethyl)benzoyl chloride → 2-Methyl-5-{[3-(trifluoromethyl)benzoyl]amino}benzoic acid

HRID 1662802Notes

Reaction equation

HRID 1662802 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18]>C1COCC1>[F:12][C:13]([F:23])([F:24])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8])=[O:18]

Participants

4

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 103746145-Amino-2-methylbenzoic acid

Product 1

HCID 596527072-Methyl-5-{[3-(trifluoromethyl)benzoyl]amino}benzoic acidYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5-amino-2-methylbenzoic acid (600 mg, 4.0 mmol) in anhydrous THF (25 mL), 3-(trifluoromethyl)benzoyl chloride (910 mg, 4.3 mmol) was added slowly. The mixture was stirred at room temperature under argon for overnight. The solvent was removed under reduced pressure and re-crystallized from acetone to afford the title compound as a white solid (600 mg, 47%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customre-crystallized from acetone

Sources & evidence

ORD record
ord-c7a53035920e4833b079b9473f57b1f9
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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