Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → HCID 54168616, compound

HRID 1081568Notes

Reaction equation

HRID 1081568 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.[CH3:20][C:21](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:22]>N1C=CC=CC=1>[C:21]([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])[CH3:20]

Participants

4

Reactant 2

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 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 arthydride (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 chloroformmethanol to yield pure 3-(4'-acetoxyphenyl)methylene-2,1-benzisothiazoline-2,2-dioxide (80% yield).

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 chloroformmethanol

Sources & evidence

ORD record
ord-199ac59d21cd4fd39153aafdf7d6fb5d
Source dataset
uspto-grants-1996_12
Patent number
US05587385

Reaction notes

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