Methyl iodide → [3-(Benzylsulfanyl)phenyl]methylcyanamide

HRID 556759Notes

Reaction equation

[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18](N(C(C)C)CC)(C)C.CI>C(#N)C>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([N:15]([CH3:18])[C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 82.5 °C

Procedure

To a solution of 3-(benzylthio)phenylcyanamide (0.80 g, 3.33 mmol) dissolved in acetonitrile (8 mL) was added diisopropylethylamine (0.65 g, 5.0 mmol), followed by addition of methyl iodide (0.94 g, 6.66 mmol). The reaction mixture was refluxed at 80-85° C. for 3 hours. After removal of solvents the residue was taken by dichloromethane (40 ml) and the organic solution was washed by water (40 ml). After dried over MgSO4 and filtered, dichloromethane solution was then concentrated in vacuo to afford yellow oil as crude product. Purification by column chromatography (SiO2, Hexane/CH2Cl2, 50% to 100%) to afford 3-(benzylthio)phenyl-N-methylcyanamide as a pale yellow oil (0.67, 80% yield): CH2Cl2 Rf=0.45; 1H-NMR (CDCl3) δ (ppm) 7.3-6.8 (m, 9H, Ar—H), 4.06 (s, S—CH2, 2H), 3.57 (s, 3H, N—CH3).

Workup

customAfter removal of solvents the residue
washthe organic solution was washed by water (40 ml)
dry with materialAfter dried over MgSO4
filtrationfiltered
concentrationdichloromethane solution was then concentrated in vacuo
customto afford yellow oil as crude product
customPurification by column chromatography (SiO2, Hexane/CH2Cl2, 50% to 100%)

Sources & evidence

ORD record: ord-cb1b9ed4654748c4ac8d0e5920d58402
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058311B2

Reaction notes

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