Hydrogen Peroxide → 5-Amino-3-(4-nitrophenyl)isothiazole-4-carbonitrile

HRID 227617Notes

Reaction equation

HRID 227617 reaction equation
[NH2:1]/[C:2](/[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[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]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[C:3]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 59099563(2z)-3-Amino-2-cyano-3-(4-nitrophenyl)prop-2-enethioamide

Product 1

HCID 690551855-Amino-3-(4-nitrophenyl)isothiazole-4-carbonitrileYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of Example 96D (23 g, 9.26 mmol) in ethanol (100 mL) was treated with 31% H2O2 (2 mL, 1.85 mmol), stirred at room temperature overnight, poured into ice water, and filtered. The filter cake was washed with water and dried to provide 2.2 g (96% yield) of the desired product. MS(ESI(−)) m/e 245 (M−H)−.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water
  3. customdried

Sources & evidence

ORD record
ord-28102a87a99b45adacc2af2fa4632385
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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