Water → HCID 13800162, compound

HRID 1906941Notes

Reaction equation

HRID 1906941 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:9]1[Cl:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH2:28]([NH2:31])[CH2:29][NH2:30]>>[ClH:26].[ClH:26].[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:9]1[NH:30][CH2:29][CH2:28][NH2:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 3301EthylenediamineHCID 13442939HCID 13442939, compound

Product 1

HCID 13800162HCID 13800162, compound

Procedure

A suspension of 1-benzyl-2-chloro-3-phenylsulfonylindole (1.0 g, 2.6 mmol) in ethylene diamine (10 ml) was heated at 80° for 1 hour. Water was added to the solution and the aqueous phase was decanted from the gummy material which separated after standing for 20 min. To this gum was added excess ethereal hydrogen chloride followed by dichloromethane. The gelatinous solid which formed was collected by filtration, washed with ethyl acetate and dried to give a solid. This solid was recrystallized from dichloromethane to give the title compound.

Workup

  1. temperaturewas heated at 80° for 1 hour
  2. customthe aqueous phase was decanted from the gummy material which
  3. customseparated
  4. additionTo this gum was added excess ethereal hydrogen chloride
  5. customThe gelatinous solid which formed
  6. filtrationwas collected by filtration
  7. washwashed with ethyl acetate
  8. customdried
  9. customto give a solid
  10. customThis solid was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-b08de1f6f7a6447aa917f253c4ea2e5b
Source dataset
uspto-grants-1987_03
Patent number
US04654360

Reaction notes

Loading…