Potassium thiocyanate → HCID 178527845, compound

HRID 900731Notes

Reaction equation

HRID 900731 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.[S-:12][C:13]#[N:14].[K+]>O>[N:9]1[CH:10]=[CH:11][C:6]([C:4]2[N:14]=[C:13]([SH:12])[NH:2][CH:3]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 2228161751746-83-9

Product 1

HCID 178527845HCID 178527845, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-1-pyridin-4-yl-ethanone hydrochloride (0.75 g, 4.348 mMol) was dissolved in water (15 mL), and to clear yellow solution was added potassium thiocyanate (0.7 g, 7.203 mMol). The mixture was heated to reflux for 4.0 h during which period HPLC showed complete disappearance of starting material. On cooling to room temperature, a yellow solid precipitate formed, which was collected by filtration. The solid was then re-suspended in a saturated solution of NaHCO3 (30 mL), stirred at room temperature for 0.5 h, and the resulting free base thiol was collected by filtration. The solid was dried under vacuum to yield 576 mg (59%) of a fluorescent yellow solid. MS(ES) 178 (M+H)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4.0 h during which period HPLC
  3. customa yellow solid precipitate formed
  4. filtrationwhich was collected by filtration
  5. filtrationthe resulting free base thiol was collected by filtration
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-ddff7a0be1664111a3fa3873a8a04194
Source dataset
uspto-grants-2008_04
Patent number
US07361669B2

Reaction notes

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