Hydrogen Peroxide → HCID 21399274, compound

HRID 1438852Notes

Reaction equation

HRID 1438852 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([S:11][CH3:12])[C:7]=1[C:13](=[O:15])[NH2:14])=[O:4].[OH:16]O>OO.C(O)(=O)C>[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([S:11]([CH3:12])=[O:16])[C:7]=1[C:13](=[O:15])[NH2:14])=[O:4]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 18550870HCID 18550870, compound

Product 1

HCID 21399274HCID 21399274, compound

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4.9 g of 1-methyl-3-(4-carbamoyl-3-(methylthio)-5-isothiazolyl)urea and 20 ml of acetic acid was heated to 95° and to the hot mixture was added dropwise 2.2 ml of 30% hydrogen peroxide. The mixture became homogeneous, but solid began to appear again after a few minutes. The mixture was maintained at 95° for two hours and then 9 drops of 30% hydrogen peroxide were added. After heating was continued an additional hour, thin-layer chromatographic analysis indicated that the reaction was completed. The mixture was cooled to -5°; the solid was isolated, washed with cold water and dried to give 4.7 g of 1-methyl-3-(4-carbamoyl-3-(methylsulfinyl)-5-isothiazolyl)urea; m.p. above 355°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas heated to 95° and to the hot mixture
  2. waitto appear again after a few minutes
  3. temperatureThe mixture was maintained at 95° for two hours
  4. temperatureAfter heating
  5. waitwas continued an additional hour
  6. temperatureThe mixture was cooled to -5°
  7. customthe solid was isolated
  8. washwashed with cold water
  9. customdried

Sources & evidence

ORD record
ord-7113d10369624685a6f94359e82104f1
Source dataset
uspto-grants-1977_11
Patent number
US04057416

Reaction notes

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