Formaldehyde → 2-Methyl-4-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-1,2,4-triazolidin-3-one

HRID 435893Notes

Reaction equation

HRID 435893 reaction equation
[CH3:1][N:2]([C:4]([NH:6][C:7]1[S:8][C:9]([C:12]([F:15])([F:14])[F:13])=[N:10][N:11]=1)=[O:5])[NH2:3].[CH2:16]=O.[OH-].[K+]>CO>[CH3:1][N:2]1[C:4](=[O:5])[N:6]([C:7]2[S:8][C:9]([C:12]([F:15])([F:13])[F:14])=[N:10][N:11]=2)[CH2:16][NH:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 214546042-Methyl-4-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)semicarbazide

Product 1

HCID 214546072-Methyl-4-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-1,2,4-triazolidin-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

The 2-methyl-4-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)semicarbazide prepared in Example 2 was dissolved in methanol (100 ml) in a glass reaction flask equipped with a mechanical stirrer and thermometer. Aqueous formaldehyde (12 ml; 37% concentration) was then added to the flask with stirring. The reaction mixture warmed to a temperature of about 35° C. Sufficient aqueous potassium hydroxide was then added to adjust the pH of the reaction medium to from about 7 to 8. A solid precipitate was formed. The precipitate was then recovered by filtration, was recrystallized from an ethyl acetate-heptane mixture and was dried under vacuum to yield the desired product 2-methyl-4-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-1,2,4-triazolidin-3-one having a melting point of 187° to 188° C.

Workup

  1. customequipped with a mechanical stirrer
  2. customA solid precipitate was formed
  3. filtrationThe precipitate was then recovered by filtration
  4. customwas recrystallized from an ethyl acetate-heptane mixture
  5. customwas dried under vacuum

Sources & evidence

ORD record
ord-666b1faadd784c4fb744a503169abfc1
Source dataset
uspto-grants-1977_02
Patent number
US04007031

Reaction notes

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