Triethylamine → 4-Fluoro-N-methoxy-N-methylbenzamide

HRID 42553Notes

Reaction equation

HRID 42553 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([N:3]([O:4][CH3:5])[CH3:2])=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 140693474-Fluoro-N-methoxy-N-methylbenzamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

In a volumetric flask N,O-dimethylhydroxylamine hydrochloride (25.54 g, 261.8 mmol) and CH2Cl2 (443 mL) were introduced under argon atmosphere at 0° C. 4-Fluorobenzoyl chloride (34.59 g, 218.2 mmol) was added followed by the slow addition of triethylamine (48.13 g, 475.6 mmol). The reaction was stirred for 30 min at 5° C. and allowed to reach room temperature. It was washed with 5% aqueous citric acid (180 mL) and with 5% aqueous NaHCO3 (180 mL). The aqueous phase was extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated to dryness, to afford 20.23 g of the desired compound (yield: 88%).

Workup

  1. customto reach room temperature
  2. washIt was washed with 5% aqueous citric acid (180 mL) and with 5% aqueous NaHCO3 (180 mL)
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b5430241ca054addb501da89600fe738
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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