Acetic Anhydride → HCID 54168616, compound

HRID 1684098Notes

Reaction equation

HRID 1684098 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][S:10]2(=[O:19])=[O:18])=[CH:4][CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][S:10]2(=[O:19])=[O:18])=[CH:4][CH:3]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54210420HCID 54210420, compound

Product 1

HCID 54168616HCID 54168616, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled solution of 3-(4'-hydroxyphenyl)methylene-2,1-benzisothiazoline-2,2-dioxide (273 mg, 1 mmol) in dry pyridine (0.5 ml) is added acetic anhydride (204 mg, 2 mmol) and the mixture maintained at 0°-5° C. overnight. Thereupon the mixture is concentrated under vacuum, the residue dissolved in dichloromethane, the organic layer washed with water and then evaporated under reduced pressure. The crude product is crystallized from chloroform-methanol to yield pure 3-(4'-acetoxyphenyl)methylene-2,1-benzisothiazoline-2,2-dioxide (80% yield). C16H13NO4S calcd: C 60.94 H 4.15 N 4.44 S 10.17 found: C 60.85 H 4.05 N 4.34 S 10.19 MS (m/z): 315

Workup

  1. temperaturethe mixture maintained at 0°-5° C. overnight
  2. concentrationThereupon the mixture is concentrated under vacuum
  3. dissolutionthe residue dissolved in dichloromethane
  4. washthe organic layer washed with water
  5. customevaporated under reduced pressure
  6. customThe crude product is crystallized from chloroform-methanol

Sources & evidence

ORD record
ord-6ecc2777f08946f08cf3d0bbd6c1c35f
Source dataset
uspto-grants-1997_06
Patent number
US05639884

Reaction notes

Loading…