Ethyl Acetate → 5,6-Dimethoxy-1,2-benzisothiazoline-1,1-dioxide

HRID 259534Notes

Reaction equation

HRID 259534 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:15][CH3:16])=[CH:5][C:6]2[S:10](=[O:12])(=[O:11])[NH:9][C:8](=O)[C:7]=2[CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Al+3].[OH-].[OH-]>O1CCCC1.O.Cl>[CH3:1][O:2][C:3]1[C:4]([O:15][CH3:16])=[CH:5][C:6]2[S:10](=[O:12])(=[O:11])[N:9]=[CH:8][C:7]=2[CH:14]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10176082Aluminum HydroxideHCID 21226445Aluminium lithium hydride2×HCID 470031361,2-Benzisothiazol-3(2H)-one, 5,6-dimethoxy-, 1,1-dioxide

Product 1

HCID 681175355,6-Dimethoxy-1,2-benzisothiazoline-1,1-dioxide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7 gm (288 millimols) of the compound obtained in step (c) were refluxed for 2 hours with 3.3 gm (865 millimols) of lithium aluminum hydride in 400 ml of tetrahydrofuran. After cooling, the excess lithium aluminum hydride was decomposed by addition of ethyl acetate, the mixture was diluted with water, and subsequently 2 N hydrochloric acid was added until the aluminum hydroxide precipitate was dissolved. The reaction solution now extracted with ethyl acetate, and the organic phase was washed with water, dried and evaporated in vacuo. The residue was digested in ether, and the desired compound was suction-filtered off.

Workup

  1. temperatureAfter cooling
  2. dissolutionwas dissolved
  3. extractionThe reaction solution now extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated in vacuo
  7. filtrationthe desired compound was suction-filtered off

Sources & evidence

ORD record
ord-09dd617fbedb4af9bd22c2ea4c78bb3e
Source dataset
uspto-grants-1977_07
Patent number
US04038407

Reaction notes

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