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

HRID 1439335Notes

Reaction equation

HRID 1439335 reaction equation
[NH2:1][C:2]([O:9][CH:10]([CH3:12])[CH3:11])=[C:3]([C:7]#[N:8])[C:4](=[S:6])[NH2:5].OO>C(O)(C)C>[NH2:5][C:4]1[S:6][N:1]=[C:2]([O:9][CH:10]([CH3:12])[CH3:11])[C:3]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 859269193-Amino-2-cyano-3-isopropoxy-2-propenethioamide

Product 1

HCID 213968055-Amino-4-cyano-3-isopropoxyisothiazoleYield 89.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In the manner of Example V C, 123 g of 3-amino-2-cyano-3-isopropoxy-2-propenethioamide in 500 ml of isopropanol were treated with 80 ml of 30% hydrogen peroxide (22.6 g of active H2O2). The residue from the reaction was recrystallized from toluene to yield 108.4 g of 5-amino-4-cyano-3-isopropoxyisothiazole, mp 146°-148°. The nmr and ir spectra were consistent with the assigned structure.

Workup

  1. customThe residue from the reaction was recrystallized from toluene

Sources & evidence

ORD record
ord-1641ec3055594fe4aeab508bd6de24af
Source dataset
uspto-grants-1977_11
Patent number
US04059433

Reaction notes

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