Methane → HCID 21396807, compound

HRID 1439326Notes

Reaction equation

HRID 1439326 reaction equation
[NH2:1][C:2]([O:9][CH2:10][CH2:11][CH3:12])=[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]([O:9][CH2:10][CH2:11][CH3:12])[C:3]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 297MethaneHCID 784Hydrogen PeroxideHCID 85906196HCID 85906196, compound

Product 1

HCID 21396807HCID 21396807, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 111 g of 3-amino-2-cyano-3-propoxypropene-thioamide in 250 ml of ethanol was heated to reflux. To this stirred mixture was added 20.4 g of 30% hydrogen peroxide, at such a rate as to maintain a uniform rate of reflux. After complete addition, the reaction mixture was heated under reflux for 20 minutes. A quantity of activated charcoal was added to the reaction mixture. The reaction mixture was filtered hot and allowed to cool. The filtrate was poured into 1500 ml of water, and the solid precipitate was collected by filtration. The dried solid was recrystallized from toluene, to give 104.5 g of 5-amino-4-cyano-3-propoxyisothiazole, m.p. 122°-125°.

Workup

  1. temperaturewas heated to reflux
  2. temperatureat such a rate as to maintain a uniform rate
  3. temperatureof reflux
  4. additionAfter complete addition
  5. temperaturethe reaction mixture was heated
  6. temperatureunder reflux for 20 minutes
  7. filtrationThe reaction mixture was filtered hot
  8. temperatureto cool
  9. additionThe filtrate was poured into 1500 ml of water
  10. filtrationthe solid precipitate was collected by filtration
  11. customThe dried solid was recrystallized from toluene

Sources & evidence

ORD record
ord-45ae10aa13c442d1978445655465de9c
Source dataset
uspto-grants-1977_11
Patent number
US04059433

Reaction notes

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