Water → 1-(4-Chlorobenzoylamino)-2-(2-methylphenyl)ethane

HRID 1156861Notes

Reaction equation

HRID 1156861 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10].[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.O>N1C=CC=CC=1>[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH3:10])=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 20638682-Methylphenethylamine

Product 1

HCID 128518081-(4-Chlorobenzoylamino)-2-(2-methylphenyl)ethaneYield 70.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Amino-2-(2-methylphenyl)ethane (13.5 g) was dissolved in 80 ml of pyridine. While the solution was cooled with stirring, 18 g of 4-chlorobenzoyl chloride was added dropwise. They were reacted at room temperature for 5 hours. Pouring of the reaction mixture into cold water gave a precipitate of crystals. The crystals were washed in water, dried, and recrystallized from cyclohexane to afford 19.2 g of 1-(4-chlorobenzoylamino)-2-(2-methylphenyl)ethane having a melting point of 95° to 96° C.

Workup

  1. temperatureWhile the solution was cooled
  2. customThey were reacted at room temperature for 5 hours
  3. customgave a precipitate of crystals
  4. washThe crystals were washed in water
  5. customdried
  6. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-1ddc2eae867c406eb390e7c827b70d3e
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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