Benzoyl isothiocyanate → N-Pyrazinylthiourea

HRID 1951172Notes

Reaction equation

HRID 1951172 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([N:16]=[C:17]=[S:18])(=O)C1C=CC=CC=1>C(O)C>[N:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:2]=1[NH:1][C:17]([NH2:16])=[S:18]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 78747Aminopyrazine

Product 1

HCID 2771013N-Pyrazinylthiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Aminopyrazine (2 g, 21.03 mmol) is dissolved in ethanol (20 ml) and benzoylisothiocyanate (2.82 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 (30 ml) and heated under reflux for 1 hour. The resultant suspension is filtered and the solid washed with water and a little cold methanol. The solid is dried in vacuo to yield the titled compound, m.p. 239-239.5° C., MH+ (AP+): 138 (M+—NH3). Other thioureas used are either commercially available or prepared in an analogous manner from the appropriate starting amine

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent is removed in vacuo
  3. dissolutionthe resulting solid dissolved in 1M sodium hydroxide (30 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-e168f899215b4c769a514ad75f2e6323
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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