Potassium Permanganate → HCID 22750023, compound

HRID 2164100Notes

Reaction equation

HRID 2164100 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[NH2:7][S:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=2)[N:12]([CH3:20])[C:11]=1[C:21]([O:23]CC)=O)=[O:9]>O.CC(C)=O>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]2[N:12]([CH3:20])[C:11]3[C:21](=[O:23])[NH:7][S:8](=[O:9])(=[O:2])[C:10]=3[C:18]=2[CH:17]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 22749947HCID 22749947, compound

Product 1

HCID 22750023HCID 22750023, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 15.8 gm (0.1 mols) of potassium permanganate in 300 ml of water was added dropwise over a period of 2.5 hours to a solution of 37.6 gm (0.125 mols) of ethyl 3-aminosulfinyl-5-chloro-1-methyl-indole-2-carboxylate in 2500 ml of acetone at 20° C. After stirring overnight at room temperature, the precipitate which had formed was filtered off and washed with warm water and acetone. The filtrate then was evaporated in vacuo at 25°-30° C. to a volume of about 350 ml. The crystallized product, ethyl 5-chloro-1-methyl-3-sulfamoyl-indole-2-carboxylate, was filtered off, washed with water and dried. Yield: 30.5 gm (77% of theory); M.p.: 207°-208° C. After acidification of the filtrate to pH 3, another product, 7-chloro-4-methyl-2H-isothiazolo[4,5-b]indole-3-(4H)-one-1,1-dioxide, was obtained, which was filtered off, washed with water and dried. Yield: 3.9 gm (12% of theory); M.p.: 288° C. (decomposition).

Workup

  1. customthe precipitate which had formed
  2. filtrationwas filtered off
  3. washwashed with warm water and acetone
  4. customThe filtrate then was evaporated in vacuo at 25°-30° C. to a volume of about 350 ml
  5. filtrationThe crystallized product, ethyl 5-chloro-1-methyl-3-sulfamoyl-indole-2-carboxylate, was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d2c137438be14a69a2b1db08cb256c50
Source dataset
uspto-grants-1979_01
Patent number
US04137313

Reaction notes

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