Ethanol → 5-Amino-3-isopropylisothiazole-4-carbonitrile

HRID 437698Notes

Reaction equation

HRID 437698 reaction equation
[NH2:1][C:2]([CH:9]([CH3:11])[CH3:10])=[C:3]([C:7]#[N:8])[C:4](=[S:6])[NH2:5].C(O)C.OO>O>[NH2:5][C:4]1[S:6][N:1]=[C:2]([CH:9]([CH3:11])[CH3:10])[C:3]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 73793209HCID 73793209, compound

Product 1

HCID 152801535-Amino-3-isopropylisothiazole-4-carbonitrileYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 444.3 g of 3-amino-2-cyano-4-methyl-2-pentenethioamide (from part B) and 1315 ml of ethanol were added dropwise 298 g of 30% hydrogen peroxide (containing 89.4 g of active H2O2) during 1.25 hours. The reaction temperature was maintained at 30°-35° with an ice bath. The reaction mixture was stirred an additional 17.5-18 hours in an ambient temperature water bath. The reaction mixture was poured into 5100 ml of cold water with stirring. The water was cooled in an ice-water bath during addition of the reaction mixture. The mixture was stirred for one hour at 5°-10° and filtered. The filter cake was washed with 2 liters of water and allowed to dry on the suction filter. After air-drying over a weekend, 426.5 g of 5-amino-4-cyano-3-isopropylisothiazole, mp 130°-132° was obtained.

Workup

  1. temperatureThe reaction temperature was maintained at 30°-35° with an ice bath
  2. stirringwith stirring
  3. stirringThe mixture was stirred for one hour at 5°-10°
  4. filtrationfiltered
  5. washThe filter cake was washed with 2 liters of water
  6. customto dry on the suction
  7. filtrationfilter
  8. customAfter air-drying over a weekend

Sources & evidence

ORD record
ord-6d6f07613d974b9199090137aec53b60
Source dataset
uspto-grants-1977_06
Patent number
US04032321

Reaction notes

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