Chloroacetone → HCID 22750055, compound

HRID 2164088Notes

Reaction equation

HRID 2164088 reaction equation
[S:1]1(=[O:15])(=[O:14])[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[C:3](=[O:13])[NH:2]1.Cl[CH2:17][C:18](=[O:20])[CH3:19]>CS(C)=O>[CH2:17]([N:2]1[C:3](=[O:13])[C:4]2[NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]=2[S:1]1(=[O:15])=[O:14])[C:18]([CH3:19])=[O:20]

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 22749971HCID 22749971, compound

Product 1

HCID 22750055HCID 22750055, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The starting compounds of the formula VI can, for example, be obtained from an alkali metal salt of a 2H-isothiazolo[4,5-b]-indole-3(4H)-one-1,1-dioxide of the formula Xa by reaction with a halo-acetone, such as chloroacetone, in dimethylsulfoxide and at a temperature of 100° to 150° C., to form a corresponding 2-acetonyl-2H-isothiazolo[4,5-b]indol-3(4H)-one-1,1-dioxide. This compound is then subjected to a base-catalyzed rearrangement reaction in the presence of 2 to 3 equivalents of an alkali metal alcoholate, which yields a 3-acetyl-2,5-dihydro-4-hydroxy-1,2-thiazino[5,6-b]-indole-1,1-dioxide of the formula ##STR12## wherein R2 and Y have the meanings defined above.

Sources & evidence

ORD record
ord-8d441250e6b1441faa65af409365677c
Source dataset
uspto-grants-1979_01
Patent number
US04137313

Reaction notes

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