Potassium ethanethioate → HCID 46916461, compound

HRID 2045937Notes

Reaction equation

Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4].[C:22]([O-:25])(=[S:24])[CH3:23].[K+]>C(#N)C.C(OC(=O)C)C>[C:22](=[O:25])([S:24][CH2:2][C:3](=[O:4])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)[CH3:23]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-bromo-N-(3-(quinoxalin-2-yl)phenyl)acetamide (300 mg, 0.876 mmol) and potassium thioacetate (400 mg, 3.5 mmol) in acetonitrile (15 mL) was heated in microwave at 140° C. for 10 min. The dark red solution was diluted with ethylacetate (50 mL), washed with brine (2×50 mL), dried over sodium sulphate, the solvent was evaporated in vacuo and the residue was purified by flash column chromatography (Flash Master, 20 g Isolute Silica column, gradient 0 to 5 min hexane, then ethyl acetate up to 50% over 20 min) to afford S-2-oxo-2-(3-(quinoxalin-2-yl)phenylamino)ethyl ethanethioate (40 mg, 13% yield). LCMS calculated for C18H15N3O2S (M+H): 338.40. found 338. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.45 (1H, br.), 9.50 (1H, s), 8.51 (1H, m), 8.11-8.18 (2H, m), 8.05-8.08 (1H, m), 7.80-7.95 (3H, m), 7.55-7.60 (1H, m), 3.90 (2H, s), 2.41 (3H, s).

Workup

washwashed with brine (2×50 mL)
dry with materialdried over sodium sulphate
customthe solvent was evaporated in vacuo
customthe residue was purified by flash column chromatography (Flash Master, 20 g Isolute Silica column, gradient 0 to 5 min hexane

Sources & evidence

ORD record: ord-96913f5f374d4a8d8480c5906a5a9134
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592415B2

Reaction notes

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