Water → Carzenide

HRID 1061858Notes

Reaction equation

HRID 1061858 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[OH-:12].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:20]>>[NH2:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([C:1]([OH:20])=[O:12])=[CH:7][CH:6]=1)(=[O:10])=[O:9]

Participants

5

Reactant 4

HCID 962WaterHCID 6269P-ToluenesulfonamideHCID 14798Sodium HydroxideHCID 516875Potassium Permanganate

Product 1

HCID 8739CarzenideYield 90%

Conditions

Temperature
70 °C

Procedure

To the solution of 17.1 g (0.1 mol) of p-toluenesulfonamide prepared in Example 1, 20 g (0.5 mol) of sodium hydroxide in 300 ml of water was added in portions 20 g (0.13 mol) of potassium permanganate. The temperature raised to 70° C. spontaneously, keep the reaction mixture in 90° C. for 2 h. The mixture was then cooled and filtered, and the filtrate was acidified with HCl. The resulting precipitate was filtered, and washed with water, dried in vacuo to give the title compound (18.1 g) as white powder, yield 90%, m.p. 291-292° C.

Workup

  1. customin 90° C.
  2. customfor 2 h
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-4443d368566445e8ac28039fb6a90145
Source dataset
uspto-grants-2005_11
Patent number
US06960611B2

Reaction notes

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