Thionyl Chloride → 4H-Furo[3,2-b]indole-2-carbonyl chloride

HRID 1577631Notes

Reaction equation

HRID 1577631 reaction equation
[O:1]1[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[CH:3]=[C:2]1[C:13]([OH:15])=O.S(Cl)([Cl:18])=O>C1C=CC=CC=1>[O:1]1[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[CH:3]=[C:2]1[C:13]([Cl:18])=[O:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12377251HCID 12377251, compound

Product 1

HCID 125218364H-Furo[3,2-b]indole-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To ethyl furo[3,2-b]indole-2-carboxylate (10 g), 10% aqueous sodium hydroxide solution (100 ml) was added, then the mixture was stirred for an hour at 60° C. The resulting solution was acidified with hydrochloric acid, and the precipitate formed was collected by filtration to give furo[3,2-b]indole-2-carboxylic acid (8.5 g). To furo[3,2-b]-indole-2-carboxylic acid (8.5 g), thionyl chloride (40 ml) and benzene (50 ml) were added, the resulting solution was refluxed for 5 hours, and the excess amounts of thionyl chloride and the benzene were evaporated to give furo[3,2-b]indole-2-carbonyl chloride (7.1 g).

Workup

  1. temperaturethe resulting solution was refluxed for 5 hours
  2. customthe excess amounts of thionyl chloride and the benzene were evaporated

Sources & evidence

ORD record
ord-1265808050a7481cb70231360db7ffb2
Source dataset
uspto-grants-1981_09
Patent number
US04288596

Reaction notes

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