Dimethyl Disulfide → HCID 86630963, compound

HRID 1009059Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][O:14][CH3:15])[N:12]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH3:22][S:23]SC>C1COCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([S:23][CH3:22])=[C:11]([CH2:13][O:14][CH3:15])[N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -75 °C

Procedure

(4-Methoxymethyl-thiazol-2-yl)-carbamic acid tert-butyl ester (840 mg, 3.4 mmol) was dissolved in dry THF (21 mL). At ˜−75° C. was added dropwise n-butyllithium solution 1.6 M in hexanes. (8.6 ml, 13.7 mmol). The dark-red mixture was stirred at ˜−75° C. for 30 min. At ˜−70° C. was then added dropwise methyl disulfide (970 mg, 10.3 mmol). The resultant yellow colored mixture was slowly warmed to rt and further stirred overnight. After quenching the reaction with saturated ammonium chloride solution, the organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. After purification on silica gel with ethyl acetate and n-heptaene as eluents the title compound was obtained as a light yellow solid. (630 mg, 59%) MS (ISP): m/e 291.3 (M−H)+

Workup

temperatureThe resultant yellow colored mixture was slowly warmed to rt and further stirred overnight
customAfter quenching
customthe reaction with saturated ammonium chloride solution
washthe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customAfter purification on silica gel with ethyl acetate and n-heptaene as eluents the title compound
customwas obtained as a light yellow solid

Sources & evidence

ORD record: ord-08f1bd78856e4a7fafe05473585f8f02
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973051B2

Reaction notes

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