Acetic Acid → HCID 178441961, compound

HRID 1105656Notes

Reaction equation

HRID 1105656 reaction equation
Cl.C(C#N)(=O)[C:3]([CH3:6])([CH3:5])[CH3:4].[C:10]([OH:13])(=O)[CH3:11].[NH2:14][NH:15][C:16]([NH:18][NH2:19])=[S:17]>O>[NH2:19][N:18]1[C:10](=[O:13])[C:11]([C:3]([CH3:4])([CH3:5])[CH3:6])=[N:14][N:15]=[C:16]1[SH:17]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 313Hydrochloric Acid2×HCID 945273,3-Dimethyl-2-oxobutanenitrileHCID 2724189Thiocarbohydrazide

Product 1

HCID 178441961HCID 178441961, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Hydrogen chloride gas was passed into a mixture of 222 g (2 mol) of pivaloyl cyanide and 120 g (2 mol) of glacial acetic acid under 8 bars and at 20° to 25° C. for four hours. Thereafter, the mixture was let down and excess glacial acetic acid was stripped off in vacuo. The product was then added to a mixture of 212 g (2 mol) of thiocarbohydrazide, 840 g of water and 280 g of concentrated hydrochloric acid. When the addition had ended, the reaction mixture was warmed to 90° C. for 1.5 hours and then subsequently stirred at room temperature overnight. The mixture was then cooled to 0° C. and the solid obtained was filtered off, washed with 400 ml of cold water and dried at 40° C. in vacuo. 314.4 g (78.6% of theory) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one (VII) of melting point 205°-209° C. were obtained.

Workup

  1. additionWhen the addition
  2. temperatureThe mixture was then cooled to 0° C.
  3. customthe solid obtained
  4. filtrationwas filtered off
  5. washwashed with 400 ml of cold water
  6. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-e199b54dc98a490e96957d9c77a6679b
Source dataset
uspto-grants-1982_01
Patent number
US04309538

Reaction notes

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