Tetrahydrofuran → HCID 58459243, compound

HRID 2036570Notes

Reaction equation

HRID 2036570 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])[N:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3SC)[C:6]=2[CH:24]=1.O[O:26][S:27]([O-:29])=O.[K+].[CH2:31]1COCC1>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])[N:7]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[S:27]([CH3:31])(=[O:29])=[O:26])[C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 58459162HCID 58459162, compound

Product 1

HCID 58459243HCID 58459243, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of N-(1-(6-fluoro-1-(2-(methylthio)phenyl)-1H-benzo[d]imidazol-2-yl)ethyl)acetamide (1.1697 g, 3.41 mmol) in THF (25.5 mL) and water (8.52 mL) was added oxone (5.23 g, 8.52 mmol) and the mixture was stirred at rt. After 48 h, to the mixture was added water (50 mL), extracted with DCM (50 mL×2). The combined organic layers were dried over Na2SO4, filtered, combined with the white solid, and concentrated under reduced pressure to give N-(1-(6-fluoro-1-(2-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-2-yl)ethyl)acetamide as an orange solid: LC-MS (ESI) m/z 376.0 [M+H]+. The orange solid was carried on crude without purification.

Workup

  1. extractionextracted with DCM (50 mL×2)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53a69967e3c04936bbb1bda3fd56540b
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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