Sulfuric Acid → HCID 178441961, compound

HRID 1065106Notes

Reaction equation

HRID 1065106 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C(C#N)(=O)[C:9]([CH3:12])([CH3:11])[CH3:10].S(=O)(=O)(O)O.[NH2:21][NH:22][C:23]([NH:25][NH2:26])=[S:24]>Cl>[NH2:26][N:25]1[C:5](=[O:7])[C:6]([C:9]([CH3:10])([CH3:11])[CH3:12])=[N:21][N:22]=[C:23]1[SH:24]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 945273,3-Dimethyl-2-oxobutanenitrileHCID 2724189Thiocarbohydrazide

Product 1

HCID 178441961HCID 178441961, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

First 5.12 kg (50 mols) of acetic anhydride and then 2.78 kg (25 mols) of pivaloyl cyanide were introduced, in each case at room temperature, into 9.81 kg (100 mols) of concentrated sulphuric acid which had been initially introduced into the reaction vessel. After subsequently stirring this reaction mixture for 2 hours, it was stirred into a solution of 2.66 kg (25 mols) of thiocarbohydrazide in 30 liters of 1 N HCl at 20°-30° C. When the addition had ended, the mixture was subsequently stirred for a further 2 hours at 50°-55° C.; after cooling, the reaction product which had precipitated was filtered off, washed with 20 liters of water and dried. 4.80 kg (96% of theory) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one (V) were obtained as colorless crystals of melting point 212°-214° C.; content, according to determination by gas chromatography, >99%.

Workup

  1. additionhad been initially introduced into the reaction vessel
  2. additionWhen the addition
  3. stirringthe mixture was subsequently stirred for a further 2 hours at 50°-55° C.
  4. temperatureafter cooling
  5. customthe reaction product which had precipitated
  6. filtrationwas filtered off
  7. washwashed with 20 liters of water
  8. customdried

Sources & evidence

ORD record
ord-3c873689f3964675ace2629abda8e109
Source dataset
uspto-grants-1982_05
Patent number
US04328340

Reaction notes

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