Methyl iodide → Methyl 4-cyclobutyl-2-ethyl-5-(imino(methylthio)methyl)benzoate
Reaction equation
[C:1]([C:4]1[C:5]([CH:16]2[CH2:19][CH2:18][CH2:17]2)=[CH:6][C:7]([CH2:14][CH3:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[S:3])[NH2:2].I[CH3:21]>O1CCCC1>[CH:16]1([C:5]2[C:4]([C:1](=[NH:2])[S:3][CH3:21])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:14][CH3:15])[CH:6]=2)[CH2:17][CH2:18][CH2:19]1Participants
4
Procedure
To a round-bottom flask was added a solution of methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoate (compound 181.6, 1.50 g, 5.41 mmol, 1.00 equiv) in tetrahydrofuran (30 mL). This was followed by the addition of iodomethane (3.80 g, 26.8 mmol, 5.00 equiv) dropwise with stirring. The resulting solution was stiffed at 25° C. for 15 h, then concentrated in vacuo. This resulted in 1.80 g (97%) of the title compound as a yellow oil.