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

HRID 1487945Notes

Reaction equation

HRID 1487945 reaction equation
[C:1]([C:4]1[C:5]([CH:15]2[CH2:18][CH2:17][CH2:16]2)=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[S:3])[NH2:2].I[CH3:20]>C1COCC1>[CH:15]1([C:5]2[C:4]([C:1](=[NH:2])[S:3][CH3:20])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:14])[CH:6]=2)[CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86672531Methyl 5-carbamothioyl-4-cyclobutyl-2-methylbenzoate2×

Product 1

HCID 68288420Methyl 4-cyclobutyl-5-(imino(methylthio)methyl)-2-methylbenzoateYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round-bottom flask was added methyl 5-carbamothioyl-4-cyclobutyl-2-methylbenzoate (compound 78.1, 861 mg, 3.27 mmol) in THF (10 mL). Iodomethane (400 μL, 6.42 mmol) was added drop-wise and the reaction mixture was stirred at room temperature for 7 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel flash chromatography (ethyl acetate to ethyl acetate/methanol=95/5) to yield the title compound as a yellowish oil (807 mg, 89% yield). m/z (ES+) 278 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 7.67 (s, 1H), 7.40 (s, 1H), 3.88-3.71 (m, 4H), 2.57 (s, 3H), 2.44 (s, 3H), 2.22-2.19 (m, 2H), 2.12 (m, 2H), 1.98-1.86 (m, 1H), 1.82-1.70 (m. 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel flash chromatography (ethyl acetate to ethyl acetate/methanol=95/5)

Sources & evidence

ORD record
ord-58b2346ddc444de395f161f16abe8cd5
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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