5-CHLORO-2-METHOXYPHENYL ISOTHIOCYANATE

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. This addition lead to an exothermic reaction to rise from room temperature to 35° C to consume the last of the thiol After a further 10 minutes the solution was evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: β-Benzylmercaptopropionitrile was prepared according to the procedure of Example 1 using α-toluenethiol (25.0 g; 0.20 moles), acrylonitrile (10.6 g; 0.20 moles) and sodium methoxide (0.5 g).