Acrylonitrile → HCID 13911551, compound

HRID 653530Notes

Reaction equation

HRID 653530 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([NH:16][NH2:17])[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:18](#[N:21])[CH:19]=[CH2:20]>[O-]CC.[Na+]>[NH2:21][C:18]1[CH2:19][CH2:20][N:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:11]=2)[N:17]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 12891839(3-(Benzyloxy)phenyl)hydrazine hydrochloride

Product 1

HCID 13911551HCID 13911551, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

To an ethanolic sodium ethoxide solution (prepared from 0.29 g of sodium and 20 mL of ethanol) was added 2 g of 3-benzyloxyphenylhydrazine hydrochloride and 0.51 g of acrylonitrile. The reaction mixture was refluxed for 5 h and then cooled to room temperature. Solvent was removed in vacuo, residue washed well with water and ether to give 0.4 g of solid. Recrystallization from CH2C12 -Hexane gave 0.3 g of pure product: mp 135°-136° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customSolvent was removed in vacuo, residue
  3. washwashed well with water and ether

Sources & evidence

ORD record
ord-fe61df9729cf4ba28f0bc3f4782e7ef7
Source dataset
uspto-grants-1987_06
Patent number
US04677210

Reaction notes

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