Methyl iodide → Methyl 4-cyclobutyl-2-ethyl-5-(imino(methylthio)methyl)benzoate

HRID 541302Notes

Reaction equation

HRID 541302 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]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86672532Methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoate2×

Product 1

HCID 68288599Methyl 4-cyclobutyl-2-ethyl-5-(imino(methylthio)methyl)benzoateYield 114.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f58290a3a984e5cacc93e5bbd7aa69d
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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