Formaldehyde → 2-Ethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)-1,2,4-triazolidin-3-one

HRID 1579474Notes

Reaction equation

HRID 1579474 reaction equation
[CH2:1]([N:3]([C:5]([NH:7][C:8]1[S:9][C:10]([CH3:13])=[N:11][N:12]=1)=[O:6])[NH2:4])[CH3:2].[CH2:14]=O.[OH-].[K+]>CO>[CH2:1]([N:3]1[C:5](=[O:6])[N:7]([C:8]2[S:9][C:10]([CH3:13])=[N:11][N:12]=2)[CH2:14][NH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 214546481-Ethyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide

Product 1

HCID 214546102-Ethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)-1,2,4-triazolidin-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Ethyl-4-(5-methyl-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-ethyl-4-(5-methyl-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-cf343bc035fb48f89f120de55189f662
Source dataset
uspto-grants-1976_01
Patent number
US03931209

Reaction notes

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