Hydrogen Peroxide → 5-Amino-4-cyano-3-ethoxyisothiazole

HRID 1439320Notes

Reaction equation

HRID 1439320 reaction equation
[NH2:1][C:2]([O:9][CH2:10][CH3:11])=[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]([O:9][CH2:10][CH3:11])[C:3]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 859268953-Amino-2-cyano-3-ethoxypropenethioamide

Product 1

HCID 213968195-Amino-4-cyano-3-ethoxyisothiazoleYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 38 g of 3-amino-2-cyano-3-ethoxypropenethioamide (above) and 400 ml of ethanol was heated to the reflux temperature. To the hot mixture was added 26.0 ml of 30% hydrogen peroxide at a rate sufficient to maintain reflux. After addition was complete the reaction mixture was heated under reflux during one half hour. To the mixture was added 100 ml of ethanol, and reflux was continued during an additional one half hour, at which time thin-layer chromatography indicated that the reaction was complete. The reaction mixture was filtered hot. The filtrate was allowed to cool slowly overnight to give 26.0 g of 5-amino-4-cyano-3-ethoxyisothiazole; m.p. 216°-217°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas heated to the reflux temperature
  2. temperatureto maintain
  3. temperaturereflux
  4. additionAfter addition
  5. temperaturewas heated
  6. temperatureunder reflux during one half hour
  7. temperaturereflux
  8. waitwas continued during an additional one half hour, at which time thin-layer chromatography
  9. filtrationThe reaction mixture was filtered hot
  10. temperatureto cool slowly overnight

Sources & evidence

ORD record
ord-ab3d513f88624b20885bfb3dea50cf0c
Source dataset
uspto-grants-1977_11
Patent number
US04059433

Reaction notes

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