Ethylamine → N-ethyl-3-(2,5-dichlorophenoxy)benzamide

HRID 46409Notes

Reaction equation

HRID 46409 reaction equation
[CH2:1]([NH2:3])[CH3:2].[Cl:4][C:5]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:6]=1[O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=[O:12]>C(OCC)(=O)C>[CH2:1]([NH:3][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][CH:16]=[C:8]([O:7][C:6]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:5]=2[Cl:4])[CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 129417813-(2,5-Dichlorophenoxy)benzoyl chloride

Product 1

HCID 12941782N-ethyl-3-(2,5-dichlorophenoxy)benzamideYield 90.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Ethyl acetate (50 ml) was added to 1.4 g of an aqueous ethylamine solution (70%), and an ethyl acetate solution containing 3.0 g of 3-(2,5-dichlorophenoxy)benzoic acid chloride was dropwise added thereto with stirring, during which the reaction mixture was cooled in an ice bath. After the addition was finished, the mixture was stirred for 1 hour at room temperature. The reaction mixture was washed with 1 N hydrochloric acid, water, 1% aqueous sodium hydroxide solution and water saturated with sodium chloride in this order and dried over anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation to obtain 3.1 g of crude crystals. On recrystallizing the crude crystals from a benzene-hexane mixed solvent, 2.8 g of N-ethyl-3-(2,5-dichlorophenoxy)benzamide were obtained. Melting point, 74.5°-75.5° C. Elementary analysis: Calcd. for C15H13Cl2NO2 : C, 58.08%; H, 4.22%, N, 4.52%; Cl, 22.86%. Found: C, 58.16%; H, 4.25%, N, 4.49%; Cl, 22.97%. NMR: δCCl 4: 1.15 (t 3H), 3.34 (quintet 2H), 6.65-7.61 (8H).

Workup

  1. additionwas dropwise added
  2. temperaturewas cooled in an ice bath
  3. additionAfter the addition
  4. stirringthe mixture was stirred for 1 hour at room temperature
  5. washThe reaction mixture was washed with 1 N hydrochloric acid, water, 1% aqueous sodium hydroxide solution and water saturated with sodium chloride in this order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThereafter, the solvent was removed by evaporation
  8. customto obtain 3.1 g of crude crystals
  9. customOn recrystallizing the crude crystals from a benzene-hexane mixed solvent

Sources & evidence

ORD record
ord-3eb50a2e3d724e2f905ddf1d0faf113e
Source dataset
uspto-grants-1979_11
Patent number
US04173464

Reaction notes

Loading…