Hydrogen Peroxide → 5-Amino-4-cyano-3-(methylthio)isothiazole

HRID 1438848Notes

Reaction equation

HRID 1438848 reaction equation
[NH2:1][C:2]([S:9][CH3:10])=[C:3]([C:7]#[N:8])[C:4](=[S:6])[NH2:5].OO>C(O)C>[NH2:5][C:4]1[S:6][N:1]=[C:2]([S:9][CH3:10])[C:3]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 85930039HCID 85930039, compound

Product 1

HCID 213992845-Amino-4-cyano-3-(methylthio)isothiazoleYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of 18.7 g of 3-amino-2-cyano-3-(methylthio)propenethioamide in 100 ml of ethanol was heated under reflux, as 14 ml (4.1 g) of 30% hydrogen peroxide were added dropwise. The exothermic reaction kept the system under reflux. The solution was heated under reflux for 30 minutes. The reaction mixture was allowed to cool to ambient temperature while it was stirred overnight. The white solid was collected by filtration to give 16.4 g of 5-amino-4-cyano-3-(methylthio)isothiazole; m.p. 188°-189°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. additionwere added dropwise
  2. customThe exothermic reaction
  3. temperatureunder reflux
  4. temperatureThe solution was heated
  5. temperatureunder reflux for 30 minutes
  6. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-1e8a9ce3475344ec94f642aabde14a9a
Source dataset
uspto-grants-1977_11
Patent number
US04057416

Reaction notes

Loading…