Reaction #53321

Reaction equation

Iodomethane

4-cyanophenyl-thiourea

→

methyl N′-(4-cyanophenyl)-carbamimidothioate

Yield 84.0%

Solvents

acetone

Conditions

Workup

1. 1
   FiltrationThe precipitate was filtered off
2. 2
   Otherdried
3. 3
   workup.DISSOLUTIONdissolved in DCM
4. 4
   WashThe organic solution was washed with NH3 (aq.) (excess)
5. 5
   Dryingdried with potassium carbonate
6. 6
   Filtrationfiltered
7. 7
   Otherthe solvent was evaporated

Procedure

Iodomethane (1.76 ml) was added to 4-cyanophenyl-thiourea (5.0 g) in acetone (100 ml). The reaction mixture was stirred overnight at RT. The precipitate was filtered off, dried and dissolved in DCM. The organic solution was washed with NH3 (aq.) (excess), dried with potassium carbonate, filtered, and the solvent was evaporated, yielding 4.53 g (84%, white solid) of methyl N′-(4-cyanophenyl)-carbamimidothioate (intermediate 6).

Source