Pyridine → Benzamide, 2-fluoro-N-methoxy-N-methyl-3-(trifluoromethyl)-

HRID 735436Notes

Reaction equation

HRID 735436 reaction equation
[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C(Cl)=O.Cl.[CH3:22][NH:23][O:24][CH3:25].N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:23]([O:24][CH3:25])[CH3:22])=[O:5]

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5180022-Fluoro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 11196047Benzamide, 2-fluoro-N-methoxy-N-methyl-3-(trifluoromethyl)-Yield 81.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Ten grams (10 g 65 mmol) of 2-fluoro-3-(trifluoromethyl)benzoic acid and oxalyl chloride in 10 mL of anhydrous CH2Cl2 were treated with a few drops of DMF, and stirred at ambient temperature for 1 hour (gas evolution ceased). N,O-Dimethyhydroxylamine hydrochloride (16.8 g, 174 mmol) was added followed by 16 ml of pyridine. The reaction mixture was stirred overnight, then washed successively with H2O, 2 N HCl, and brine. The resulting solution was dried over sodium sulfate. Evaporation of solvents in vacuo gave 13.3 g of product as an oil, which was pure enough to be used in the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. washwashed successively with H2O, 2 N HCl, and brine
  3. dry with materialThe resulting solution was dried over sodium sulfate
  4. customEvaporation of solvents in vacuo

Sources & evidence

ORD record
ord-1e552925c9964dc999bcf070173862a5
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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