Methyl iodide → methyl N'-(4-cyanophenyl)carbamimidothioate

HRID 270623Notes

Reaction equation

HRID 270623 reaction equation
I[CH3:2].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH2:14])=[S:13])=[CH:7][CH:6]=1)#[N:4]>CC(C)=O>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]=[C:12]([S:13][CH3:2])[NH2:14])=[CH:9][CH:10]=1)#[N:4]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2757973(4-Cyanophenyl)thiourea

Product 1

HCID 13748458methyl N'-(4-cyanophenyl)carbamimidothioateYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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).

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried
  3. dissolutiondissolved in DCM
  4. washThe organic solution was washed with NH3 (aq.) (excess)
  5. dry with materialdried with potassium carbonate
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cc177943ede343319750c72a1105e24b
Source dataset
uspto-grants-2008_11
Patent number
US07449575B2

Reaction notes

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