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

HRID 67032Notes

Reaction equation

HRID 67032 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-5136ff6a939d437e995cdac9c239e277
Source dataset
uspto-grants-1982_08
Patent number
US04344790

Reaction notes

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