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

HRID 541273Notes

Reaction equation

HRID 541273 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 152.5, 861 mg, 3.27 mmol) in THF (10 mL). Iodomethane (912 mg, 6.42 mmol) was added dropwise and the reaction mixture was stiffed at room temperature for 7 hours. The reaction mixture was concentrated in vacuo and purified by SiO2 flash chromatography (ethyl acetate to ethyl acetate/methanol=95/5) to afford methyl 4-cyclobutyl-5-(imino(methylthio)methyl)-2-methylbenzoate 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 in vacuo
  2. custompurified by SiO2 flash chromatography (ethyl acetate to ethyl acetate/methanol=95/5)

Sources & evidence

ORD record
ord-996eb769ac2f4d5288869ec625d14e8d
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…