Ammonia → HCID 21283489, compound

HRID 1500808Notes

Reaction equation

HRID 1500808 reaction equation
[S:1]1[C:5]2[C:6](O)=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[C:12](=[O:15])([O-])[O-].[K+].[K+].I[CH3:19].N>CC(C)=O.CO>[CH3:19][O:10][C:8]1[CH:7]=[C:6]([O:15][CH3:12])[C:5]2[S:1][CH:2]=[CH:3][C:4]=2[CH:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86687877HCID 86687877, compound

Product 1

HCID 21283489HCID 21283489, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-benzothiophene-5,7-diol (1.16 g, 6.98 mmol) in acetone (20 ml) under argon were added potassium carbonate (2.89 g, 20.9 mmol) and iodomethane (912 μl, 14.6 mmol). The resulting mixture was stirred under reflux for 18 h. After cooling to rt, the mixture was treated with a 7 M solution of ammonia in methanol (10 ml) for 30 min and then adsorbed on silica gel. Purification by column chromatography over silica gel (cyclohexane/ethyl acetate 40:1) afforded 0.52 g (32% of th.) of the title compound.

Workup

  1. temperatureunder reflux for 18 h
  2. customPurification by column chromatography over silica gel (cyclohexane/ethyl acetate 40:1)

Sources & evidence

ORD record
ord-e8c5b2723b614cd5a7d50b8dfe18c4df
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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