Indole → 3,4-Dichloro-5-(1H-indol-3-yl)furan-2(5H)-one

HRID 355167Notes

Reaction equation

HRID 355167 reaction equation
[C:1]([OH:9])(=[O:8])/[C:2](=[C:4](\[CH:6]=O)/[Cl:5])/[Cl:3].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1>C1C=CC=CC=1>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH:6]2[O:9][C:1](=[O:8])[C:2]([Cl:3])=[C:4]2[Cl:5])=[CH:11]1

Participants

4

Reactant 2

HCID 798IndoleHCID 2771871Mucochloric Acid

Product 1

HCID 204427033,4-Dichloro-5-(1H-indol-3-yl)furan-2(5H)-oneYield 16.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 20.3 g (0.12 mole) of mucochloric acid, 14.1 g (0.12 mole) of indole and 125 ml of benzene was heated for approximately twenty hours at reflux temperature. The reaction mixture was cooled to ambient temperature and a dark brown solid which had separated was collected by filtration. This solid was purified by two successive recrystallizations from benzene at approximately 60° C., with the aid of decolorizing charcoal. After the second recrystallization, the purified product was dried at 60° C. in vacuo to obtain 5.3 g of the known 5-(3-indolyl)-3,4-dichloro-2(5H)-furanone (Formula VI: R=R1 =Y=H), a pale green-colored solid, which first melted at 174° C., then turned black and finally decomposed at 182° C.

Workup

  1. temperaturewas heated for approximately twenty hours
  2. temperatureat reflux temperature
  3. customa dark brown solid which had separated
  4. filtrationwas collected by filtration
  5. customThis solid was purified by two successive recrystallizations from benzene at approximately 60° C., with the aid of decolorizing charcoal
  6. customAfter the second recrystallization
  7. customthe purified product was dried at 60° C. in vacuo

Sources & evidence

ORD record
ord-8660c133b6d441a68b026c9c1e3ff419
Source dataset
uspto-grants-1983_03
Patent number
US04377698

Reaction notes

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