Dimethyl Sulfide → HCID 86723692, compound

HRID 577459Notes

Reaction equation

[Cl:1]NC(=O)CCC(N)=O.CSC.[CH2:13]([O:20][C:21]1[C:26]([CH2:27]O)=[C:25]([CH2:29][CH3:30])[CH:24]=[C:23]([CH3:31])[N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl.[Cl-].[Na+].O>[CH2:13]([O:20][C:21]1[C:26]([CH2:27][Cl:1])=[C:25]([CH2:29][CH3:30])[CH:24]=[C:23]([CH3:31])[N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a 0° C. solution of N-chloro succinamide (81.5 mg, 0.598 mmol) in dichloromethane (2.47 mL) was added dimethyl sulfide (48 ul, 0.653 mmol). The reaction mixture was then cooled to −20° C. and a solution of [2-(benzyloxy)-4-ethyl-6-methylpyridin-3-yl]methanol (Cpd DD, 140 mg, 0.554 mmol) in dichloromethane (1 mL) was added drop wise. After 2 hours the reaction mixture was poured into brine (5 mL) then extracted with dichloromethane (10 mL). The organic layer was dried over sodium sulfate, filtered, then concentrated under vacuum. The residue was purified by column chromatography (heptane/EtOAc) to give the title compound (Cpd EE, 35 mg, 23% yield) as a colorless oil. 1H NMR (chloroform-d) δ 7.52 (d, J=7.3 Hz, 2H), 7.29-7.44 (m, 3H), 6.65 (s, 1H), 5.46 (s, 2H), 4.74 (s, 2H), 2.72 (q, J=7.6 Hz, 2H), 2.44 (s, 3H), 1.28 (t, J=7.6 Hz, 3H).

Workup

extractionthen extracted with dichloromethane (10 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified by column chromatography (heptane/EtOAc)

Sources & evidence

ORD record: ord-40f22ee1630b457380f1e6667ef53a29
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040515B2

Reaction notes

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