tert-Butanol → Benzo[b]thiophene-7-acetamide

HRID 557188Notes

Reaction equation

HRID 557188 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][C:11]#[N:12])[C:2]1=2.CC([OH:17])(C)C.[OH-].[K+]>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][C:11]([NH2:12])=[O:17])[C:2]1=2

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium Hydroxide2×HCID 11446611Benzo[b]thiophene-7-acetonitrile

Product 1

HCID 17985839Benzo[b]thiophene-7-acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add benzo[b]thiophene-7-acetonitrile (1.9 g, 11.0 mmol) to 2-methyl-2-propanol (20 mL). Heat to reflux under nitrogen and add potassium hydroxide pellets (7.4 g, 132 mmol). Stir and reflux under nitrogen for 30 minutes. Pour solution off of the excess potassium hydroxide and dilute with ethyl acetate. Wash with a 1:1 mixture of aqueous saturated sodium chloride, aqueous saturated sodium hydrogen carbonate. Dry the organic phase over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Rinse the solid with cold diethyl ether and dry under vacuum to obtain the title compound as an off-white solid.

Workup

  1. temperatureHeat
  2. temperatureto reflux under nitrogen
  3. temperaturereflux under nitrogen for 30 minutes
  4. washWash with a 1:1 mixture of aqueous saturated sodium chloride, aqueous saturated sodium hydrogen carbonate
  5. dry with materialDry the organic phase over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. washRinse the solid with cold diethyl ether
  9. customdry under vacuum

Sources & evidence

ORD record
ord-1dd578f621154e49beb1906f19f56efc
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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