Chloroform → 5-Bromo-6-methylsulfamoylindole

HRID 2290185Notes

Reaction equation

HRID 2290185 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11](=[O:15])(=[O:14])[NH:12][CH3:13])[NH:7][CH2:6][CH2:5]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(Cl)(Cl)Cl>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11](=[O:15])(=[O:14])[NH:12][CH3:13])[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 140245865-Bromo-6-methylsulfamoylindoline

Product 1

HCID 140245875-Bromo-6-methylsulfamoylindole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-bromo-6-methylsulfamoylindoline, 55.92 g (0.19 mol) in 150 ml dioxane was added 41.79 gm (0.184 mol) of 2,3-dichloro-5,6-dicyanobenzoquinone at 25° C. The resulting brown solution was heated to 80° C. for 2 hours when thin layer chromatography using chloroform showed that the reaction was complete. The reaction mixture was allowed to cool, filtered through Celite and the filtrate concentrated under reduced pressure. The resulting brown solid was stirred in a mixture of methylene chloride/ether 50/50 and then filtered. This procedure was carried out two additional times and gave 35.2 g (63.9% by weight yield) of 5-bromo-6-methylsulfamoylindole.

Workup

  1. temperatureto cool
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate concentrated under reduced pressure
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1f466149ba114b248a7797fff3f2f799
Source dataset
uspto-grants-1986_10
Patent number
US04615966

Reaction notes

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