Ammonia → 6-chloro-3-oxo-2,3-dihydro-1H-indene-5-sulfonamide

HRID 65932Notes

Reaction equation

HRID 65932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11](Cl)(=[O:13])=[O:12])[C:7](=[O:15])[CH2:6][CH2:5]2.[NH3:16]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11](=[O:13])(=[O:12])[NH2:16])[C:7](=[O:15])[CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 221190346-chloro-3-oxo-2,3-dihydro-1H-indene-5-sulfonyl chloride

Product 1

HCID 227563846-chloro-3-oxo-2,3-dihydro-1H-indene-5-sulfonamide

Procedure

99.6 Grams of 5-chloro-6-chlorosulfonyl-1-indanone are introduced portionwise into 700 ml of liquid ammonia. The solvent is allowed to evaporate and the residue is dissolved in water, is heated within a short time on the water-bath and is filtered after the addition of active charcoal. The solution is acidified with hydrochloric acid to a pH of 2, the precipitate is filtered off with suction and is washed with water. The melting point of 5-chloro-6-sulfamoyl-1-indanone is in the range of from 205° to 208° C., and after recrystallization from a mixture of acetone and water it is 216° to 218° C.

Workup

  1. customto evaporate
  2. dissolutionthe residue is dissolved in water
  3. temperatureis heated within a short time on the water-bath
  4. filtrationis filtered
  5. additionafter the addition of active charcoal
  6. filtrationthe precipitate is filtered off with suction
  7. washis washed with water
  8. customis in the range of from 205° to 208° C.
  9. customafter recrystallization
  10. additionfrom a mixture of acetone and water it
  11. customis 216° to 218° C.

Sources & evidence

ORD record
ord-2122063c84c848c19820fb2b2aa12265
Source dataset
uspto-grants-1978_12
Patent number
US04129656

Reaction notes

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