Formaldehyde → 4-(5-Methoxy-1,3,4-thiadiazol-2-yl)-2-propyl-1,2,4-triazolidin-3-one

HRID 435902Notes

Reaction equation

HRID 435902 reaction equation
[CH2:1]([N:4]([C:6]([NH:8][C:9]1[S:10][C:11]([O:14][CH3:15])=[N:12][N:13]=1)=[O:7])[NH2:5])[CH2:2][CH3:3].[CH2:16]=O.[OH-].[K+]>CO>[CH2:1]([N:4]1[C:6](=[O:7])[N:8]([C:9]2[S:10][C:11]([O:14][CH3:15])=[N:12][N:13]=2)[CH2:16][NH:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 21454627N-(5-Methoxy-1,3,4-thiadiazol-2-yl)-1-propylhydrazine-1-carboxamide

Product 1

HCID 214546464-(5-Methoxy-1,3,4-thiadiazol-2-yl)-2-propyl-1,2,4-triazolidin-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Propyl-4-(5-methoxy-1,3,4-thiadiazol-2-yl)-semicarbazide (0.1 mole) dissolved in methanol (100 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. Aqueous formaldehyde (0.2 mole; 37% concentration) is then added to the reaction vessel with stirring. Dilute aqueous potassium hydroxide is added to the reaction mixture to adjust the pH to between 7 and 8 and stirring is continued for a period of about 20 minutes resulting in the formation of a solid precipitate. The precipitate is recovered by filtration, is recrystallized and is dried under vacuum to yield the desired product 2-propyl-4-(5-methoxy-1,3,4-thiadiazol-2-yl)-1,2,4-triazolidin-3-one.

Workup

  1. additionis charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. stirringstirring
  4. customresulting in the formation of a solid precipitate
  5. filtrationThe precipitate is recovered by filtration
  6. customis recrystallized
  7. customis dried under vacuum

Sources & evidence

ORD record
ord-bb350c565cd54f499b21be07950a3cc5
Source dataset
uspto-grants-1977_02
Patent number
US04007031

Reaction notes

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