Thionyl Chloride → N-Chloromethylisatin

HRID 231032Notes

Reaction equation

HRID 231032 reaction equation
O[CH2:2][N:3]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[C:4]1=[O:5].S(Cl)([Cl:16])=O>>[Cl:16][CH2:2][N:3]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[C:4]1=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 39834Indole-2,3-dione, 1-(hydroxymethyl)-

Product 1

HCID 12207287N-Chloromethylisatin

Procedure

N-Hydroxymethylisatin (10 g, 0.056 mol) was added to thionyl chloride (100 ml) and the mixture was heated under reflux for 2 hours. N-Chloromethylisatin (about 11 g) was obtained by distilling the remaining thionyl chloride under reduced pressure. The melting point was 121° to 123° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-5334c4e95c64423ba49a5bf357cb5e8e
Source dataset
uspto-grants-1989_07
Patent number
US04845020

Reaction notes

Loading…