Ammonia → 3-Bromo-5-(trifluoromethyl)benzamide

HRID 1257381Notes

Reaction equation

HRID 1257381 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:6](O)=[O:7].C[N:16](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.N>CN(C)C=O.O>[Br:12][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:11]=1)[C:6]([NH2:16])=[O:7]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 110867883-Bromo-5-(trifluoromethyl)benzoic acid

Product 1

HCID 593165253-Bromo-5-(trifluoromethyl)benzamideYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution (18 mL) of 3-trifluoromethyl-5-bromobenzoic acid (5.0 g, 19 mmol) in N,N-dimethylformamide were added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (4.3 g, 22 mmol), 1-hydroxybenzotriazole (3.4 g, 22 mmol) and 28% aqueous ammonia (1.7 mL, 28 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was to recrystallized (hexane-ethyl acetate) to give the title compound (3.7 g, 74%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto recrystallized (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-141da9acc2e34218b9043930da62c582
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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