Acrylonitrile → HCID 70477006, compound

HRID 464000Notes

Reaction equation

HRID 464000 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[C:22](#[N:25])[CH:23]=[CH2:24].C1CCN2C(=NCCC2)CC1>ClCCl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:24][CH2:23][C:22]#[N:25])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53846385HCID 53846385, compound

Product 1

HCID 70477006HCID 70477006, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 100 ml of a solution of 6.0 g of N-(p-chlorobenzoyl)phenylglycine methyl ester in dichloromethane were added 1.6 g of acrylonitrile and 3.6 g of 1,8-diazabicyclo[5.4.0]-7-undecene followed by stirring at room temperature for 16 hours. The solvent was distilled off and 100 ml of ethyl ether were added to the resulting residue. The mixture was washed with two 100 ml portions of water, and the organic layer was separated off and dried over magnesium sulphate. The solvent was distilled off and the residue was recrystallized from diethyl ether, to give 5.8 g of the desired product as a colourless powder melting at 127°-128° C.

Workup

  1. distillationThe solvent was distilled off
  2. addition100 ml of ethyl ether were added to the resulting residue
  3. washThe mixture was washed with two 100 ml portions of water
  4. customthe organic layer was separated off
  5. dry with materialdried over magnesium sulphate
  6. distillationThe solvent was distilled off
  7. customthe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-6dd883738cb84d718a9f24d4edb43818
Source dataset
uspto-grants-1985_10
Patent number
US04545942

Reaction notes

Loading…