3-Acetyl-2,5-dihydro-4-hydroxy-5-methyl-1,2-thiazino[5,6-b]indole-1,1-dioxide → HCID 22749974, compound

HRID 2164089Notes

Reaction equation

HRID 2164089 reaction equation
C([C:4]1[NH:5][S:6](=[O:20])(=[O:19])[C:7]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]([CH3:16])[C:8]=2[C:17]=1[OH:18])(=O)C>C(O)CO.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:16][N:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:7]2[S:6](=[O:20])(=[O:19])[NH:5][CH2:4][C:17](=[O:18])[C:8]1=2

Participants

5

Reactant 1

HCID 227500043-Acetyl-2,5-dihydro-4-hydroxy-5-methyl-1,2-thiazino[5,6-b]indole-1,1-dioxide

Product 1

HCID 22749974HCID 22749974, compound

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 174Ethylene GlycolSolventHCID 241BenzeneSolvent

Procedure

The acetyl derivates of the formula XII are treated in the presence of an acid and under anhydrous conditions with ethyleneglycol and form the ketals of the formula ##STR13## wherein R2 and Y have the meanings defined above. For example, 3-acetyl-2,5-dihydro-4-hydroxy-5-methyl-1,2-thiazino[5,6-b]indole-1,1-dioxide is refluxed with ethyleneglycol in benzene as a solvent and in the presence of p-toluenesulfonic acid as a catalyst for 5 days, which yields the ethylene ketal of 2,5-dihydro-5-methyl-1,2-thiazino[5,6-b]indole-4(3H)-one-1,1-dioxide.

Sources & evidence

ORD record
ord-6cb6a8a8061a455b922beb312ed36c06
Source dataset
uspto-grants-1979_01
Patent number
US04137313

Reaction notes

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