Propanenitrile, 3-[(3-methylphenyl)amino]- → N-(2-cyanoethyl)-3-methylcarbanilic acid-[3-(trichloromethylcarbonylamino)-phenyl]-ester

HRID 1262787Notes

Reaction equation

HRID 1262787 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1)#[N:2].[Cl:13][C:14]([Cl:29])([Cl:28])[C:15]([NH:17][C:18]1[CH:19]=[C:20]([O:24][C:25](Cl)=[O:26])[CH:21]=[CH:22][CH:23]=1)=[O:16]>C(#N)C>[Cl:13][C:14]([Cl:28])([Cl:29])[C:15]([NH:17][C:18]1[CH:19]=[C:20]([O:24][C:25](=[O:26])[N:5]([CH2:4][CH2:3][C:1]#[N:2])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=2)[CH:21]=[CH:22][CH:23]=1)=[O:16]

Participants

4

Reactant 2

HCID 119683Propanenitrile, 3-[(3-methylphenyl)amino]-HCID 53923320HCID 53923320, compound

Product 1

HCID 20455825N-(2-cyanoethyl)-3-methylcarbanilic acid-[3-(trichloromethylcarbonylamino)-phenyl]-ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Into a solution of 16.0 g N-(2-cyanoethyl)-3-methylaniline in 100 ml acetonitrile, 31.7 g chloroformic acid-3-(trichloromethylcarbonylamino)-phenyl ester taken up in 100 ml acetonitrile is added dropwise. The reaction mixture is heated to boiling for another 10 minutes, cooled, stirred in 500 ml ice water, the precipitate filtered and recrystallized from isopropanol.

Workup

  1. additionis added dropwise
  2. temperatureThe reaction mixture is heated
  3. temperaturecooled
  4. filtrationthe precipitate filtered
  5. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-7e0471fb381c4f49b7565e25d9c0ef91
Source dataset
uspto-grants-1984_06
Patent number
US04453973

Reaction notes

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