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

HRID 616509Notes

Reaction equation

HRID 616509 reaction equation
[NH2:1][C:2]([N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[C:3]([C:7]#[N:8])[C:4](=[S:6])[NH2:5].OO.O>C(O)C>[NH2:5][C:4]1[S:6][N:1]=[C:2]([N:9]([CH2:10][CH2:11][CH3:12])[CH2:13][CH2:14][CH3:15])[C:3]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 859420353-Amino-2-cyano-3-(dipropylamino)propenethioamide

Product 1

HCID 203675715-Amino-4-cyano-3-(dipropylamino)isothiazoleYield 73.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9.6 g of 3-amino-2-cyano-3-(dipropylamino)propenethioamide in 50 ml of ethanol was heated to reflux temperature and 5 ml of 30% hydrogen peroxide (1.4 g H2O2) were added at such a rate as to maintain reflux. After complete addition the reaction mixture was heated under reflux during 10 minutes. To the reaction mixture was added 40 ml of water, which was then allowed to cool to ambient temperature. The solid precipitate was collected by filtration, and recrystallized from acetonitrile-water, to give 7.0 g of 5-amino-4-cyano-3-(dipropylamino)isothiazole; m.p. 136°-138°. The nmr and ir spectra were consistent with the assigned structure.

Workup

  1. additionwere added at such a rate as
  2. temperatureto maintain
  3. temperaturereflux
  4. additionAfter complete addition the reaction mixture
  5. temperaturewas heated
  6. temperatureunder reflux during 10 minutes
  7. filtrationThe solid precipitate was collected by filtration
  8. customrecrystallized from acetonitrile-water

Sources & evidence

ORD record
ord-e164fc87fe7d42e6a96dc0e487751b36
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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