Ethoxyacetyl chloride → 3-Ethoxymethyl-4-methyl-1,2,4-triazoline-5-thione

HRID 27107

Reaction equation

HRID 27107 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[CH3:8][NH:9][C:10](=[S:13])[NH:11][NH2:12]>N1C=CC=CC=1>[CH2:1]([O:3][CH2:4][CH:5]1[N:9]([CH3:8])[C:10](=[S:13])[N:11]=[N:12]1)[CH3:2]

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 867332233-Ethoxymethyl-4-methyl-1,2,4-triazoline-5-thioneYield 65.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethoxyacetyl chloride (57 g) was added slowly to a stirred solution of 4-methylthiosemicarbazide (53.5 g) in dry pyridine (500 ml) at 0°-5°. The mixture was allowed to attain room temperature and stirring was continued for 18 hours. Following concentration under reduced pressure the residue was treated with a solution of sodium (21.4 g) in ethanol (500 ml) and the mixture was heated under reflux for 24 hours. Following concentration and acidification with hydrochloric acid a solid was obtained. After partial concentration the solid was collected and recrystallised from ethyl acetate to give 3-ethoxymethyl-4-methyl-1,2,4-triazoline-5-thione (53 g) m.p. 137°-138°.

Workup

  1. customto attain room temperature
  2. concentrationconcentration under reduced pressure the residue
  3. additionwas treated with a solution of sodium (21.4 g) in ethanol (500 ml)
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 24 hours
  6. concentrationconcentration and acidification with hydrochloric acid a solid
  7. customwas obtained
  8. concentrationAfter partial concentration the solid
  9. customwas collected
  10. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-61ab1667506f4159badd52211343e25e
Source dataset
uspto-grants-1980_09
Patent number
US04220652

Linked notes

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