Methyl iodide → Methyl 5-(imino(methylthio)methyl)-2,4-dimethylbenzoate

HRID 541244Notes

Reaction equation

[C:1]([C:4]1[C:5]([CH3:15])=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[S:3])[NH2:2].[CH3:16]I>O1CCCC1>[NH:2]=[C:1]([S:3][CH3:16])[C:4]1[C:5]([CH3:15])=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of methyl 5-carbamothioyl-2,4-dimethylbenzoate (compound 130.1, 3.10 g, 12.5 mmol, 1.00 equiv, 90%) in tetrahydrofuran (30 mL) was added CH3I (3.95 g, 27.8 mmol, 2.00 equiv) and the resulting mixture was stirred overnight at 25° C. The organic layer was washed with 2×30 mL of Na2S2O4 (aq.) and 1×30 mL of brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. This resulted in 2.10 g (64%) of methyl 5-(imino(methylthio)methyl)-2,4-dimethylbenzoate as a yellow oil.

Workup

washThe organic layer was washed with 2×30 mL of Na2S2O4 (aq.) and 1×30 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThis resulted in 2.10 g (64%) of methyl 5-(imino(methylthio)methyl)-2,4-dimethylbenzoate as a yellow oil

Sources & evidence

ORD record: ord-b8c822c29696434f81bb951116285bee
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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