Dimethyl Disulfide → HCID 13154244, compound

HRID 1740932Notes

Reaction equation

[C:1]([C:5]([NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[CH3:20][S:21]SC>C(OCC)C.O>[C:1]([C:5]([NH:7][C:8]1[CH:13]=[C:12]([CH2:14][S:21][CH3:20])[CH:11]=[CH:10][N:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2-tert-butylcarbonylamino-4-picoline (Step A, 250 mg) in anhydrous ethyl ether (5 mL) was cooled to -78° C. and treated with tert-butyllithium (1.7 mL, 1.7 M), and stirred at -78° C. for 3 hrs. To this was added dimethyl disulfide (0. 177 mL) and the reaction was allowed to warm to room temperature. The mixture was diluted with water and ethyl ether. The aqueous layer was extracted with ether. The combined organic layers were washed with saturated sodium chloride, dried over sodium sulfate, and concentrated in vacuo. The resulting oil was purified by medium pressure liquid chromatography on a 21×300 mm silica column eluted with 40% ethyl acetate/methylene chloride to afford the title compound (260 mg, lower Rf spot) and 2-tert-butylcarbonylamino-4-methylthiomethylpyridine (40 mg, higher Rf spot).

Workup

temperatureto warm to room temperature
extractionThe aqueous layer was extracted with ether
washThe combined organic layers were washed with saturated sodium chloride
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe resulting oil was purified by medium pressure liquid chromatography on a 21×300 mm silica column
washeluted with 40% ethyl acetate/methylene chloride

Sources & evidence

ORD record: ord-78385a36291f4b2ea9ba8c73d78299cb
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972975

Reaction notes

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