Benzoyl isothiocyanate → (6-Methoxy-pyrazin-2-yl)-thiourea

HRID 2214764Notes

Reaction equation

HRID 2214764 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[N:5][CH:4]=1.C([N:18]=[C:19]=[S:20])(=O)C1C=CC=CC=1>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][C:19]([NH2:18])=[S:20])[CH:6]=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 48681936-Methoxypyrazin-2-amine

Product 1

HCID 21948402(6-Methoxy-pyrazin-2-yl)-thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6-Methoxy-pyrazin-2-ylamine (0.85 g, 6.8 mmol) is dissolved in ethanol (7 ml) and benzoylisothiocyanate (0.91 ml) is added dropwise. The mixture is heated to 80° C. with stirring for 10 minutes then allowed to cool to room temperature. The solvent is removed in vacuo and the resulting solid dissolved in 1M sodium hydroxide (15 ml) and heated under reflux for 1 hour. The resultant suspension is filtered and the solid washed with water and a little cold ethanol. The solid is dried in vacuo to yield the title compound.

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent is removed in vacuo
  3. dissolutionthe resulting solid dissolved in 1M sodium hydroxide (15 ml)
  4. temperatureheated
  5. temperatureunder reflux for 1 hour
  6. filtrationThe resultant suspension is filtered
  7. washthe solid washed with water
  8. customThe solid is dried in vacuo

Sources & evidence

ORD record
ord-8047c569232c418e9e7ea9481324df5a
Source dataset
uspto-grants-2006_09
Patent number
US07109202B2

Reaction notes

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