Hydrogen Sulfide → 3-Phenyl-1,2-thiazol-5-amine

HRID 332830Notes

Reaction equation

HRID 332830 reaction equation
[NH2:1]/[C:2](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH:3]\[C:4]#[N:5].[SH2:12]>CCO.C1COCC1>[C:6]1([C:2]2[CH:3]=[C:4]([NH2:5])[S:12][N:1]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 1711920Aminocinnamonitrile

Product 1

HCID 126038793-Phenyl-1,2-thiazol-5-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-3-amino-3-phenylacrylonitrile (95 mg, 0.660 mmol) in EtOH (1.0 mL) and THF (1.0 mL) in a sealed tube, H2S gas was bubbled through for 5 min. It was then stirred at 90 C for 20 h. The mixture was concentrated in vacuo. The residue was dissolved in MeOH (2.0 mL), aq. H2O2 (30%, 0.5 mL) was added. After being stirred at room temperature for 2 min, the reaction was completed. The mixture was concentrated in vacuo. The residue was purified by HPLC to give 3-phenylisothiazol-5-amine (22 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH (2.0 mL)
  3. additionaq. H2O2 (30%, 0.5 mL) was added
  4. stirringAfter being stirred at room temperature for 2 min
  5. concentrationThe mixture was concentrated in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-6f37c16098894801bdc4de5b3e2ad39d
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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