Carbon Disulfide → HCID 178506378, compound

HRID 452806

Reaction equation

HRID 452806 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]([NH:21][NH2:22])=[O:20])[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.C(N(CC)CC)C.[C:32](=S)=[S:33].[Cl-].[NH4+]>C(O)C>[F:24][C:2]([F:23])([F:1])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:20][C:32]([SH:33])=[N:22][N:21]=4)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 686643883-[3-(Trifluoromethoxy)phenyl]-1-benzofuran-5-carbohydrazide

Product 1

HCID 178506378HCID 178506378, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the obtained 3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-carbohydrazide, triethylamine (5.6 mL, 40.4 mmol), carbon disulfide (18.2 mL, 303 mmol) and ethanol (70 mL) was heated under reflux for 5 hr. After cooling, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/2) and recrystallized from hexane/ethyl acetate to give 5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole-2-thiol.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hr
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/2)
  9. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-fba1d2cc8d5d4287b2273c83ed9c279d
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Linked notes

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