Formaldehyde → 2-n-Butyl-4-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-1,2,4-triazolidin-3-one

HRID 435908Notes

Reaction equation

HRID 435908 reaction equation
[CH2:1]([N:5]([C:7]([NH:9][C:10]1[S:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[N:13][N:14]=1)=[O:8])[NH2:6])[CH2:2][CH2:3][CH3:4].[CH2:19]=O.[OH-].[K+]>CO>[CH2:1]([N:5]1[C:7](=[O:8])[N:9]([C:10]2[S:11][C:12]([S:15]([CH3:18])(=[O:16])=[O:17])=[N:13][N:14]=2)[CH2:19][NH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 214546252-n-Butyl-4-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)semicarbazide

Product 1

HCID 214546262-n-Butyl-4-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-1,2,4-triazolidin-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-n-Butyl-4-(5-methylsulfonyl-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 to 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-n-butyl-4-(5-methylsulfonyl-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-4722a68dbfb647afa08f32d718db8cdf
Source dataset
uspto-grants-1977_02
Patent number
US04007031

Reaction notes

Loading…