Hydrogen Sulfide → Isothiazolo(3,4-b)pyridin-3-amine

HRID 2200508Notes

Reaction equation

HRID 2200508 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[SH2:10]>N1C=CC=CC=1>[N:1]1[S:10][C:8]([NH2:9])=[C:7]2[CH:6]=[CH:5][CH:4]=[N:3][C:2]=12

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 8182592-Amino-3-cyanopyridine

Product 1

HCID 297118Isothiazolo(3,4-b)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-3-cyanopyridine (1.00 g, 8.40 mmol) in pyridine (8 mL) and TEA (0.8 mL) in a sealed tube, H2S gas was bubbled through for 5 min. It was then stirred at room temperature for 20 h. The mixture was concentrated in vacuo to dryness. The residue was dissolved in MeOH (10 mL). To the solution, aq. H2O2 (30%, 3 mL) was added. The mixture was then stirred at room temperature for 5 h, during which time, solids precipitated out. The solids were collected by filtration, dried on vacuum to give isothiazolo[3,4-b]pyridin-3-amine (860 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo to dryness
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. additionTo the solution, aq. H2O2 (30%, 3 mL) was added
  4. stirringThe mixture was then stirred at room temperature for 5 h, during which time, solids
  5. customprecipitated out
  6. filtrationThe solids were collected by filtration
  7. customdried on vacuum

Sources & evidence

ORD record
ord-2f774f56a30a40818cef199a5c98e94d
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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