Potassium ethanethioate → S-2-(4-Chlorophenyl)benzo[d]oxazol-5-yl ethanethioate

HRID 1896754Notes

Reaction equation

[C:1]([O-:4])(=[S:3])[CH3:2].[K+].F[B-](F)(F)F.[H+].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][C:21]3[CH:27]=[CH:26][C:25]([N+]#N)=[CH:24][C:22]=3[N:23]=2)=[CH:15][CH:14]=1>CS(C)=O.O>[C:1](=[O:4])([S:3][C:25]1[CH:26]=[CH:27][C:21]2[O:20][C:19]([C:16]3[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=3)=[N:23][C:22]=2[CH:24]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of potassium thioacetate (130 mg, 1.13 mmol) in DMSO (2.8 mL) at room temperature was added dropwise a solution of 2-(4-chlorophenyl)benzo[d]oxazole-5-diazonium tetrafluoroboric acid salt (370 mg, 1.08 mmol) in DMSO (1.4 mL). After 15 min, the mixture was heated at 70° C. for 1 h. After cooling, the mixture was diluted with water, and then extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting using a gradient (ethyl acetate/hexanes 5:95 v/v to ethyl acetate/hexanes 15:85 v/v) and triturated with diethyl ether/hexanes to afford 11.3 mg (3%) of the title compound (LCMS RT=7.89 min, MH+ 304.2)

Workup

temperatureAfter cooling
extractionextracted several times with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous MgSO4
customevaporated
customThe resulting solid was purified by column chromatography
washeluting
customtriturated with diethyl ether/hexanes

Sources & evidence

ORD record: ord-b674329b83974248ba399160ba776107
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518980B2

Reaction notes

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