Methane → HCID 53689667, compound

HRID 616513Notes

Reaction equation

HRID 616513 reaction equation
[NH2:1][C:2]([N:9]([CH2:11][CH3:12])[CH3:10])=[C:3]([C:7]#[N:8])[C:4](=[S:6])[NH2:5].OO.C>C(O)C>[NH2:5][C:4]1[S:6][N:1]=[C:2]([N:9]([CH2:11][CH3:12])[CH3:10])[C:3]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 297MethaneHCID 784Hydrogen PeroxideHCID 85942042HCID 85942042, compound

Product 1

HCID 53689667HCID 53689667, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 60 g of 3-amino-2-cyano-3-(ethylmethylamino)propenethioamide and 250 ml of ethanol was heated to reflux, while 40 ml of 30% hydrogen peroxide (11.1 g of active H2O2) were added dropwise at such a rate as to maintain an even reflux. After the peroxide addition was completed, the reaction mixture was heated for 30 minutes. Charcoal was added to the hot solution. The charcoal was removed by filtration and the filtrate was evaporated under reduced pressure. The residue was recrystallized from toluene to yield 51 g of 5-amino-4-cyano-3-(ethylmethylamino)isothiazole, mp 94°-95°. The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. additionwere added dropwise at such a rate as
  3. temperatureto maintain
  4. temperaturean even reflux
  5. temperaturethe reaction mixture was heated for 30 minutes
  6. customThe charcoal was removed by filtration
  7. customthe filtrate was evaporated under reduced pressure
  8. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-2863d33a19e14a66b73db6fcfaa4b57c
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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