Ethylene Oxide → 2-(2-hydroxyethyl)-4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide

HRID 231575Notes

Reaction equation

HRID 231575 reaction equation
[CH2:1]1[O:3][CH2:2]1.[N+:4]([C:7]1[C:12]2[C:13](=[O:18])[NH:14][S:15](=[O:17])(=[O:16])[C:11]=2[CH:10]=[CH:9][CH:8]=1)([O-:6])=[O:5]>O>[OH:3][CH2:2][CH2:1][N:14]1[C:13](=[O:18])[C:12]2[C:7]([N+:4]([O-:6])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=2[S:15]1(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 6354Ethylene OxideHCID 217943664-Nitro-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

Product 1

HCID 138812912-(2-hydroxyethyl)-4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To approximately 2 ml of ethylene oxide cooled in an ice bath was added a suspension of 4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide (2.0 g, 8.76 mmol) in H2O (140 ml). After stirring in the ice bath for 1 hour, the mixture was allowed to stir at 20-25° for 18 hours. Water was removed under reduced pressure and the residue flash chromatographed over silica gel. Elution with 2% isopropanol-98% CH2Cl2 gave product which was recrystallized from EtOAc-hexane to give the 2-hydroxethyl derivative (0.39 g, 16%), m.p. 140-1°.

Workup

  1. additionwas added
  2. customWater was removed under reduced pressure
  3. customthe residue flash chromatographed over silica gel
  4. washElution with 2% isopropanol-98% CH2Cl2
  5. customgave product which
  6. customwas recrystallized from EtOAc-hexane
  7. customto give the 2-hydroxethyl derivative (0.39 g, 16%), m.p. 140-1°

Sources & evidence

ORD record
ord-7bcacb29d1244121b8047f56cfe9f12f
Source dataset
uspto-grants-1989_07
Patent number
US04847294

Reaction notes

Loading…