3-Anilinopropionitrile → N-(2-cyanoethyl)-carbanilic acid-[3-(cyclopropylcarbonylamino)-phenyl]-ester

HRID 1262789Notes

Reaction equation

HRID 1262789 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)#[N:2].[CH:12]1([C:15]([NH:17][C:18]2[CH:19]=[C:20]([O:24][C:25](Cl)=[O:26])[CH:21]=[CH:22][CH:23]=2)=[O:16])[CH2:14][CH2:13]1>C(#N)C>[CH:12]1([C:15]([NH:17][C:18]2[CH:19]=[C:20]([O:24][C:25](=[O:26])[N:5]([CH2:4][CH2:3][C:1]#[N:2])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:21]=[CH:22][CH:23]=2)=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 141003-AnilinopropionitrileHCID 54149755Chloroformic acid-[3-(cyclopropylcarbonylamino)-phenyl]-ester

Product 1

HCID 20455829N-(2-cyanoethyl)-carbanilic acid-[3-(cyclopropylcarbonylamino)-phenyl]-ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

29.2 g N-(2-cyanoethyl)-aniline is dissolved in 200 ml acetonitrile and then reacted with 23.97 g chloroformic acid-[3-(cyclopropylcarbonylamino)-phenyl]-ester with stirring, with which the temperature of the solution rises to about 35° C. After standing overnight the solvent is removed under vacuum, the remaining oily residue is treated with water, the water is decanted and the oil brought to crystallization with a 1:1 mixture of isopropyl ether/isopropanol. The crystallizate is finally recrystallized from isopropanol.

Workup

  1. customrises to about 35° C
  2. customthe solvent is removed under vacuum
  3. additionthe remaining oily residue is treated with water
  4. customthe water is decanted
  5. customthe oil brought to crystallization with a 1:1 mixture of isopropyl ether/isopropanol
  6. customThe crystallizate is finally recrystallized from isopropanol

Sources & evidence

ORD record
ord-b8555fce5934482fbc457dabca56bf04
Source dataset
uspto-grants-1984_06
Patent number
US04453973

Reaction notes

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