Hydrochloric Acid → Buthidazolamine

HRID 261757Notes

Reaction equation

HRID 261757 reaction equation
[C:1](O)(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:8][NH:9][C:10]([NH2:12])=[S:11].P(Cl)(Cl)(Cl)=O.Cl>O1CCOCC1.O>[NH2:12][C:10]1[S:11][C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])=[N:8][N:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6417Pivalic acidHCID 24813Phosphorus oxychlorideHCID 2723789Thiosemicarbazide

Product 1

HCID 170170ButhidazolamineYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A three-liter reaction flask fitted with a power stirrer, heating mantle, dropping funnel, thermometer and water-cooled condenser was charged with 449 g (4.4 moles) of pivalic acid and 1500 ml of dioxane. To the stirred solution there was added 364 g (4.0 moles) of thiosemicarbazide. The dropping funnel was charged with 765 g (5.0 moles) of phosphorus oxychloride which was added to the well stirred solution in the reaction vessel. The reaction mixture was stirred and heated at 95°-100°. When the evolution of hydrogen chloride was complete, the mixture was cooled and the liquid phase was removed by decantation. Sufficient hot water was added to dissolve the pot residue. With ice-bath cooling and agitation, there was slowly added 450 ml of 50% aqueous sodium hydroxide. The mixture was cooled to 20° and the product was collected on a vacuum filter. The filter cake was washed with water and dried. There was obtained 404 g (64.2%) of 2-amino-5-tert-butyl-1,3,4-thiadiazole, m.p. 187°-88°.

Workup

  1. customA three-liter reaction flask
  2. customfitted with a power stirrer
  3. temperatureheating mantle
  4. additionwas added to the well
  5. stirringThe reaction mixture was stirred
  6. temperatureheated at 95°-100°
  7. temperaturethe mixture was cooled
  8. customthe liquid phase was removed by decantation
  9. additionSufficient hot water was added
  10. dissolutionto dissolve the pot residue
  11. temperatureWith ice-bath cooling
  12. temperatureThe mixture was cooled to 20°
  13. customthe product was collected on a vacuum
  14. filtrationfilter
  15. washThe filter cake was washed with water
  16. customdried

Sources & evidence

ORD record
ord-a51c1dc1ef154ba8a6a04e0402ae5fdf
Source dataset
uspto-grants-1979_05
Patent number
US04152329

Reaction notes

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