Methylamine → 4-fluoro-N-methylbenzamide

HRID 2214497Notes

Reaction equation

HRID 2214497 reaction equation
[CH3:1][NH2:2].[OH-].[Na+].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1>C(Cl)Cl>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:2][CH3:1])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 40742474-fluoro-N-methylbenzamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30 mL MeNH2 (40% wt in H2O) was added 139 mL of 1N NaOH. To this was added 130 mL of CH2Cl2 followed by 4-fluorobenzoyl chloride (22 grams, 139 mmol) while the mixture was rapidly stirred. After 1 hour the organic layer was separated, washed with H2O, dried over Na2SO4 and solvent removed under vacuum to yield 20 grams (94% yield) solid. 1H NMR (500 MHz, DMSO) δ: 2.78 (d, 3, J=5), 7.28 (t, 2, J=9), 7.91 (m, 2), 8.46 (br s, 1). 13C NMR (125 MHz, DMSO) δ: 26.13, 114.95, 115.13, 129.49, 129.56, 130.87, 130.90, 162.67, 164.64, 165.46.

Workup

  1. customAfter 1 hour the organic layer was separated
  2. washwashed with H2O
  3. dry with materialdried over Na2SO4 and solvent
  4. customremoved under vacuum

Sources & evidence

ORD record
ord-284492eb07254cdea14406c1ce51260f
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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