Methyl iodide → Methyl 3-(imino(methylthio)methyl)-4-methylbenzoate

HRID 541210Notes

Reaction equation

HRID 541210 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:7]([O:9][CH3:10])=[O:8])(=[S:3])[NH2:2].I[CH3:16]>O1CCCC1>[NH:2]=[C:1]([S:3][CH3:16])[C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 71695284Methyl 3-carbamothioyl-4-methylbenzoate2×

Product 1

HCID 68288789Methyl 3-(imino(methylthio)methyl)-4-methylbenzoateYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-carbamothioyl-4-methylbenzoate (compound 38.3, 2.10 g, 9.85 mmol, 1.00 equiv) in tetrahydrofuran (30 mL) was added iodomethane (2.8 g, 19.73 mmol, 2.00 equiv) dropwise. The resulting mixture was stirred at room temperature. After 3 h, the reaction mixture was concentrated under reduced pressure and the residue was dried under vacuum to yield 1.6 g (73%) of the title compound as a light yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-c73f6135d7714bc0974cef31ca917195
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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