Acrylonitrile → HCID 10420001, compound

HRID 374243Notes

Reaction equation

HRID 374243 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([P:8](OCC)(=[O:12])[O:9][CH2:10][CH3:11])[CH2:6][CH3:7]>C(S)CC>[CH2:10]([O:9][P:8]([CH2:5][CH2:6][CH3:7])([CH2:3][CH2:2][C:1]#[N:4])=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 140428Diethyl propanephosphonate

Product 1

HCID 10420001HCID 10420001, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 7848Propyl mercaptanSolvent

Procedure

53 g of acrylonitrile are added dropwise under nitrogen at a reaction temperature of 70° C. to a mixture of 160 g of diethyl propanephosphonate in 100 g of n-propylmercaptan in the course of 2 hours. After a further 3 hours the solvent (low-boiling solvent such as C3H7SC2H5 and excess C3H7SH) is removed by vacuum distillation; the crude product is obtained in a yield of 173 g with a 95.4% purity, which corresponds to a theoretical yield of 94.4%. The boiling point of the product is 117°-118° C. at 0.027 mbar.

Workup

  1. customAfter a further 3 hours the solvent (low-boiling solvent such as C3H7SC2H5 and excess C3H7SH) is removed by vacuum distillation

Sources & evidence

ORD record
ord-3ef0750f512f44a98ad9c07057953095
Source dataset
uspto-grants-1992_11
Patent number
US05166385

Reaction notes

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