Ammonium Hydroxide → 5-(3-Methylpentan-3-yl)-1,3,4-thiadiazol-2-amine

HRID 462360Notes

Reaction equation

HRID 462360 reaction equation
[CH2:1]([C:3]([CH3:9])([CH2:7][CH3:8])[C:4](O)=O)[CH3:2].[NH2:10][NH:11][C:12]([NH2:14])=[S:13].P(Cl)(Cl)(Cl)=O.[OH-].[NH4+]>O1CCOCC1>[NH2:14][C:12]1[S:13][C:4]([C:3]([CH2:7][CH3:8])([CH3:9])[CH2:1][CH3:2])=[N:10][N:11]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 298462-Ethyl-2-methylbutyric acidHCID 2723789Thiosemicarbazide

Product 1

HCID 132342635-(3-Methylpentan-3-yl)-1,3,4-thiadiazol-2-amineYield 91.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution containing 13.0 g of 2-ethyl-2-methylbutyric acid and 9.1 g of thiosemicarbazide in 125 ml of dioxane was stirred and heated to 90° C. To the stirred reaction mixture was added dropwise over thirty minutes 15.3 g of phosphorous oxychloride. Following complete addition, the reaction mixture was heated at 90° C. for six hours. The mixture was then cooled to abiout 30° C. and added to 100 g of ice. The aqueous mixture was made alkaline by the addition of ammonium hydroxide, and the alkaline solution was extracted several times with ethyl acetate. The extracts were combined, washed with water, dried, and the solvent was removed by evaporation under reduced pressure to afford 17.0 g of 2-amino-5-(1-ethyl-1-methylpropyl)-1,3,4-thiadiazole.

Workup

  1. customTo the stirred reaction mixture
  2. additionaddition
  3. temperaturethe reaction mixture was heated at 90° C. for six hours
  4. temperatureThe mixture was then cooled
  5. customto abiout 30° C.
  6. extractionthe alkaline solution was extracted several times with ethyl acetate
  7. washwashed with water
  8. customdried
  9. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-cfde728d9a0c4a02a90492e1a7bba845
Source dataset
uspto-grants-1985_05
Patent number
US04515625

Reaction notes

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