Ethylamine → N-ethyl-4-fluorobenzamide

HRID 44311Notes

Reaction equation

HRID 44311 reaction equation
[CH2:1]([NH2:3])[CH3:2].C(N(CC)CC)C.[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1>C(Cl)Cl.O>[CH2:1]([NH:3][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:12]([F:11])=[CH:13][CH:14]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 4693101N-ethyl-4-fluorobenzamideYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethylamine (69.4 mL, 139 mmol) and triethylamine (21.10 mL, 151 mmol) in DCM (Volume: 150 mL) was added p-fluorobenzoyl chloride (15.13 mL, 126 mmol) at 0° C. The reaction was stirred at 0° C. for 1 hr and then warmed slowly to room temperature. The reaction mixture was diluted with water. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered, and the organic phase stripped to dryness via rotary evaporation. The organic extract was dried in vacuo to provide N-ethyl-4-fluorobenzamide (21 g, 100% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12 (t, J=7.20 Hz, 3 H) 3.23-3.32 (m, 2 H) 7.24-7.33 (m, 2 H) 7.87-7.95 (m, 2 H) 8.49 (t, J=3.92 Hz, 1 H). ESI-MS: m/z 168.0 (M+H)+. mp=73.2-76.3° C.

Workup

  1. temperaturewarmed slowly to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe organic phase stripped to dryness via rotary evaporation
  7. extractionThe organic extract
  8. customwas dried in vacuo

Sources & evidence

ORD record
ord-ddaa92b1fe7844e2bd879910f97fd9b9
Source dataset
uspto-grants-2013_09
Patent number
US08541417B2

Reaction notes

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