Hydrochloric Acid → 3-Fluoro-N-methoxy-N-methylbenzamide

HRID 1428925Notes

Reaction equation

HRID 1428925 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].CCN=C=NCCCN(C)C.Cl.[CH3:23][NH:24][O:25][CH3:26].Cl>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([N:24]([O:25][CH3:26])[CH3:23])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 99683-Fluorobenzoic AcidHCID 14232N,O-DimethylhydroxylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 212657573-Fluoro-N-methoxy-N-methylbenzamideYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluorobenzoic acid (30 g, 214.1 mmol) in DCM (300 mL) were added EDC.HCl (45 g, 235 mmol) and N,O-dimethylhydroxylamine.HCl (23 g, 235 mmol) at 0° C. under N2. The reaction mixture was stirred at rt for 3 h, then diluted with water (1000 mL) and extracted with DCM (3×200 mL). The organics were washed with brine, dried over Na2SO4, and concentrated to obtain the 3-fluoro-N-methoxy-N-methylbenzamide (24 g, 61%). (183.91 [M+H]) 1H NMR: (400 MHz, CDCl3) δ: 3.38 (s, 3H), 3.57 (s, 3H), 7.14-7.19 (m, 1H), 7.37-7.43 (m, 2H), 7.48-7.50 (d, J=7.6, 1H).

Workup

  1. customat 0° C.
  2. extractionextracted with DCM (3×200 mL)
  3. washThe organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b4034fbf41704c89a726d590426ba0c7
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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