2-Amino-6-methylpyridine → (6-Methylpyridin-2-yl)thiourea

HRID 2214761Notes

Reaction equation

HRID 2214761 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.C([N:17]=[C:18]=[S:19])(=O)C1C=CC=CC=1>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:18]([NH2:17])=[S:19])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 157652-Amino-6-methylpyridineHCID 68284Benzoyl isothiocyanate

Product 1

HCID 685983(6-Methylpyridin-2-yl)thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

6-Methyl-pyridin-2-ylamine (1.0 g, 9.2 mmol) is dissolved in ethanol (10 ml) and benzoylisothiocyanate (1.24 ml, 9.2 mmol) is added dropwise. The mixture is heated to 40° 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 2 hour. The resultant suspension is filtered and the solid washed copiously with water and then with cold ethanol. The solid is dried in vacuo to yield the title compound. Mass Spec (APCI+) 168.

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 2 hour
  6. filtrationThe resultant suspension is filtered
  7. washthe solid washed copiously with water
  8. customThe solid is dried in vacuo

Sources & evidence

ORD record
ord-36d83d99e8d542d79c09334be356a2c1
Source dataset
uspto-grants-2006_09
Patent number
US07109202B2

Reaction notes

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