Hydrogen Peroxide → Thieno[3,2-c]isothiazol-3-amine

HRID 2200499Notes

Reaction equation

HRID 2200499 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[S:9])[NH2:8].OO>CO>[N:1]1[S:9][C:7]([NH2:8])=[C:3]2[S:4][CH:5]=[CH:6][C:2]=12

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 143211023-Amino-2-thiophenecarbothioamide

Product 1

HCID 818861Thieno[3,2-c]isothiazol-3-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude 3-aminothiophene-2-carbothioamide in MeOH (5 mL) was added H2O2 (30%, 0.6 mL), after stirring at room temperature for 15 min, it was concentrated to remove most of MeOH, and then diluted with EtOAC, organic layer was washed with brine, concentrated to give crude pdt, purification by column chromatography (DCM/EtOAC=3:1) gave thieno[3,2-c]isothiazol-3-amine (334 mg).

Workup

  1. concentrationit was concentrated
  2. customto remove most of MeOH
  3. additiondiluted with EtOAC, organic layer
  4. washwas washed with brine
  5. concentrationconcentrated
  6. customto give crude
  7. custompdt, purification by column chromatography (DCM/EtOAC=3:1)

Sources & evidence

ORD record
ord-282819540fdd48a7af87715042a2a4f2
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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