Acrylonitrile → 2-(4-Chloro-2-fluorophenyl)-3-(2-cyanoethylthio)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

HRID 647409Notes

Reaction equation

HRID 647409 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([SH:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1.[C:20](#[N:23])[CH:21]=[CH2:22]>O1CCOCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([S:17][CH2:22][CH2:21][C:20]#[N:23])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 132575922-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one

Product 1

HCID 132575952-(4-Chloro-2-fluorophenyl)-3-(2-cyanoethylthio)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-oneYield 60.6%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 312751,4-DioxaneSolvent

Procedure

In 15 ml of dioxane was dissolved 2.1 g of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindole-1-on, and 1.5 g of acrylonitrile, together with several drops of triethylamine, was added, followed by heating at 85° to 90° C. for 6 hours. The reaction solution was concentrated under reduced pressure, and the residual, oily substance was purified by means of column chromatography with the use of silica gel (acetone:hexane=1:3), thereby producing 1.5 g of the subject compound in white crystals, m.p. 101°-103° C.

Workup

  1. temperatureby heating at 85° to 90° C. for 6 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residual, oily substance was purified by means of column chromatography with the use of silica gel (acetone:hexane=1:3)

Sources & evidence

ORD record
ord-b12fe61b3d90422785931a30eb3296d2
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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