Ammonia → Benzo[B]thiophene-7-carboxamide

HRID 1783973Notes

Reaction equation

HRID 1783973 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([OH:12])=O)[C:2]1=2.S(Cl)(Cl)=O.[NH3:17].C([O-])(O)=O.[Na+]>ClCCl.O.CN(C=O)C>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([NH2:17])=[O:12])[C:2]1=2

Participants

8

Reactant 4

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 142350731-Benzothiophene-7-carboxylic acid

Product 1

HCID 19602336Benzo[B]thiophene-7-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of benzo[b]thiophene-7-carboxylic acid (505 mg, 2.84 mmol) in dichloromethane (10 mL) is stirred at rt and thionyl chloride (669 mg, 5.68 mmol, 2.0 equiv.) is added, followed by DMF (0.06 mL), causing gas evolution. The resulting solution is stirred at rt for 1 hour. Aqueous ammonia (10 mL) is then added cautiously to the mixture causing vigorous gas evolution. The resulting mixture is then diluted with water (50 mL), and pH is brought to neutral by adding saturated NaHCO3 (aq.). The aqueous layer is extracted with DCM, and the organic layers are combined and dried over Na2SO4. Evaporation of the solvent under reduced pressure affords the title compound (81% pure) as a yellow solid (500 mg, 98%) which is used without further purification.

Workup

  1. extractionThe aqueous layer is extracted with DCM
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1e72ea23b8e744db9713ae2ea73eeea8
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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