Pyridine → N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

HRID 887241Notes

Reaction equation

HRID 887241 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].N1C=CC=CC=1>C(Cl)Cl.C(OCC)C>[CH3:18][O:17][N:16]([CH3:15])[C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 14069348N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

4-(Trifluoromethyl)benzoyl chloride (5.0 g, 23.9 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.55 g, 26.3 mmol, 1.1 eq.) were combined in CH2Cl2 (200 mL) at 0° C. and treated with pyridine (4.3 mL, 52.6 mmol). After stirring for 2 hours, the mixture was allowed to attain ambient temperature, diluted with diethyl ether and washed with water, aqueous HCl, and water. The organic phase was separated and concentrated to provide the title compound which was used directly in the next step. 1H NMR (300 MHz, d6-DMSO) 7.90 (m, 4H), 3.52 (s, 3H), 3.28 (s, 3H); MS (DCI/NH3) m/e 234 (M+H)+.

Workup

  1. customto attain ambient temperature
  2. washwashed with water, aqueous HCl, and water
  3. customThe organic phase was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4afad5966f4c4c37b0c8d3ca9ff31bdc
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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