Water → 5-Amino-2-benzenesulfonylaminoindan

HRID 1088833Notes

Reaction equation

HRID 1088833 reaction equation
[N:1]12[CH2:11][CH2:10][CH2:9][CH:8]=[C:7]1[CH2:6][CH2:5][CH2:4][CH2:3][NH:2]2.C(Cl)Cl.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>[Cl-]>[NH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH:1][S:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:23])=[O:22])[CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 9834010Diazabicyclo[5.4.0]undec-7-ene

Product 1

HCID 148205145-Amino-2-benzenesulfonylaminoindanYield 54.3%

Reagents, catalysts & solvents 1

HCID 312ChlorideSolvent

Procedure

Into a solution of 4.0 g of this product in pyridinemethylene chloride is added 8.39 g of diazabicyclo[5.4.0]undeca-7-ene. Subsequently, under cooling, a methylene chloride solution of 3.36 g of benzenesulfonyl chloride is added dropwise with stirring. After the reaction, water is added, and the organic layer is separated, followed by evaporation of the solvent. The residue is crystallized from an ethanol-n-hexane mixture, purified through silica gel column chromatography, and recrystallized from an ethyl acetate-n-hexane mixture to give 2.98 g of 5-amino-2-benzenesulfonylaminoindan.

Workup

  1. temperatureSubsequently, under cooling
  2. additionis added
  3. customthe organic layer is separated
  4. customfollowed by evaporation of the solvent
  5. customThe residue is crystallized from an ethanol-n-hexane mixture
  6. custompurified through silica gel column chromatography
  7. customrecrystallized from an ethyl acetate-n-hexane mixture

Sources & evidence

ORD record
ord-58fb6d1ada3b44f495bbbf808470834e
Source dataset
uspto-grants-1990_10
Patent number
US04963587

Reaction notes

Loading…