Triethylamine → 2-fluoro-N-methoxy-N-methylbenzamide

HRID 406648Notes

Reaction equation

HRID 406648 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:11][NH:12][O:13][CH3:14].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:12]([O:13][CH3:14])[CH3:11])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 14232N,O-Dimethylhydroxylamine

Product 1

HCID 183575562-fluoro-N-methoxy-N-methylbenzamideYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-fluorobenzoyl chloride (50 g, 0.31 mol) in CH2Cl2 (200 mL) was added N,O-dimethylhydroxylamine (46 g, 0.47 mol), and a solution of triethylamine (127 g, 1.26 mol) in CH2Cl2 (100 mL) at 0° C. The reaction mixture was warmed slowly to rt, and stirred for 3 h. The mixture was quenched with iced water and extracted with CH2Cl2 (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford 2-fluoro-N-methoxy-N-methylbenzamide (48 g, yield: 84.6%).

Workup

  1. customat 0° C
  2. customThe mixture was quenched with iced water
  3. extractionextracted with CH2Cl2 (200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed692ae0414a44ab914e204b66cbf91a
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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