Water → 4-Fluoro-N-methoxy-N-methylbenzamide

HRID 479750Notes

Reaction equation

HRID 479750 reaction equation
Cl.[CH3:2][O:3]CN.C([N:8]([CH2:11]C)CC)C.[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.O>C(Cl)Cl>[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:8]([O:3][CH3:2])[CH3:11])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 21959107Methoxymethanamine hydrochloride

Product 1

HCID 140693474-Fluoro-N-methoxy-N-methylbenzamideYield 106.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture containing methoxymethylamine hydrochloride (44 g, 0.45 mol) and triethylamine (138 mL, 0.99 mol) in CH2Cl2 (500 mL) at 0° C. was added over 30 min, 4-fluorobenzoyl chloride (50 mL, 0.41 mol). The result-ing mixture was allowed to warm to rt and stirring was continued for 30 min, at which time the mixture was poured into H2O and extracted with Et2O. The organic extract was washed with saturated aqueous NaCl and dried (MgSO4). Removal of the solvent in vacuo afforded the title compound (80 g, 100%), which was used without further purification: 1H NMR (CDCl3): d 7.72 (dd, 2H); 7.06 (apparent t, 2H); 3.52 (s, 3H); 3.43 (s, 3H).

Workup

  1. additionwas added over 30 min
  2. extractionextracted with Et2O
  3. extractionThe organic extract
  4. washwas washed with saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-562f0cadb49342ac864323213c5db111
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

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