4-Methylbenzoyl Chloride → 1-(p-Toluoylamino)-2-(2-chlorophenyl)ethane

HRID 1156897Notes

Reaction equation

HRID 1156897 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:10].[C:11]1([CH3:20])[CH:16]=[CH:15][C:14]([C:17](Cl)=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[C:11]1([CH3:20])[CH:16]=[CH:15][C:14]([C:17]([NH:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[Cl:10])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 831172-(2-Chlorophenyl)ethylamine

Product 1

HCID 128518181-(p-Toluoylamino)-2-(2-chlorophenyl)ethaneYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Amino-2-(2-chlorophenyl)ethane (44.5 g) was dissolved in 140 ml of pyridine, and with stirring under cooling, 44.5 g of p-toluoyl chloride was added dropwise. The reaction was performed at room temperature for 3 hours. The reaction mixture was poured into ice water, and the crystals that precipitated were collected by filtration. The crystals were dissolved in benzene, washed successively with hydrochloric acid, water and saturated aqueous sodium chloride solution, and dried. The solvent was distilled off. The residue was recrystallized from benzene to afford 72 g of 1-(p-toluoylamino)-2-(2-chlorophenyl)ethane as colorless needles having a melting point of 106.0° to 108.5° C.

Workup

  1. temperatureunder cooling
  2. customthe crystals that precipitated
  3. filtrationwere collected by filtration
  4. dissolutionThe crystals were dissolved in benzene
  5. washwashed successively with hydrochloric acid, water and saturated aqueous sodium chloride solution
  6. customdried
  7. distillationThe solvent was distilled off
  8. customThe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-8cf54bb891394e5e8cf8a1bf30f5780f
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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