Water → N,N-diethyl-3-fluorobenzamide

HRID 128480Notes

Reaction equation

HRID 128480 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH2:11]([NH:13][CH2:14][CH3:15])[CH3:12].O>C1C=CC=CC=1>[CH2:11]([N:13]([CH2:14][CH3:15])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=1)[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 743763-Fluorobenzoyl chloride

Product 1

HCID 963334N,N-diethyl-3-fluorobenzamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a 50 ml flask fitted with a stirrer, condenser, drying tube and an addition funnel is added m-fluorobenzoyl chloride (15.9 g, 0.10 mole) and benzene (100 ml). Then a solution of diethylamine (14.6 g, 0.20 mole) in benzene (100 ml) is added dropwise over 1 hour and the reaction mixture allowed to stir at room temperature overnight. Water (150 ml) is then added rapidly and after trituration for a few minutes, the benzene layer is decanted and washed repeatedly with water (5×150 ml), dried (anhyd. Na2SO4) and the solvent removed under vacuum to afford 18 grams of N,N-diethyl-3-fluorobenzamide as a yellow oil. Elemental analysis calculated for C11H14FNO: C, 67.70; H, 7.22; F, 9.72; N, 7.16; Found: C, 66.40; H, 7.08; F, 9.65; N, 6.92

Workup

  1. customTo a 50 ml flask fitted with a stirrer, condenser
  2. customdrying tube and an addition funnel
  3. waitafter trituration for a few minutes
  4. customthe benzene layer is decanted
  5. washwashed repeatedly with water (5×150 ml)
  6. dry with materialdried (anhyd. Na2SO4)
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-90199355bd3f4e4fb868216329f9c134
Source dataset
uspto-grants-1981_03
Patent number
US04259510

Reaction notes

Loading…