Benzyl mercaptan → 3-(benzylsulfanyl)propanenitrile

HRID 1493292Notes

Reaction equation

HRID 1493292 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([SH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>CO.C(#N)C=C>[CH2:5]([S:12][CH2:3][CH2:2][C:1]#[N:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 7855AcrylonitrileHCID 8471Triethylamine

Product 1

HCID 2200273-(benzylsulfanyl)propanenitrileYield 97.5%

Reagents, catalysts & solvents 2

HCID 7855AcrylonitrileCatalystHCID 887MethanolSolvent

Procedure

Acrylonitrile (21.4 g) was added dropwise to a solution of benzyl mercaptan (49.6 g) and triethylamine (4 ml) in methanol (400 ml). This addition lead to an exothermic reaction and the temperature of the reaction mixture was allowed to rise from room temperature to 35° C. After 10 minutes the reaction was almost complete as shown by TLC, there being a trace of unreacted thiol still present. Additional acrylonitrile (0.5 g) was then added to consume the last of the thiol. After a further 10 minutes the solution was evaporated to give the title compound 69.0 g as a pale yellow oil.

Workup

  1. customThis addition lead to an exothermic reaction
  2. customto rise from room temperature to 35° C
  3. customto consume the last of the thiol
  4. customAfter a further 10 minutes the solution was evaporated

Sources & evidence

ORD record
ord-e6b2ef3f68cb447f90fa3a868a620fcf
Source dataset
uspto-grants-1991_06
Patent number
US05021441

Reaction notes

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