Hydrochloric Acid → HCID 178441961, compound

HRID 1763880Notes

Reaction equation

HRID 1763880 reaction equation
S(Cl)Cl.[CH3:4][C:5](=O)[C:6]([CH3:9])([CH3:8])[CH3:7].Cl.CNC.[OH-:15].[Na+].[NH2:17][NH:18][C:19]([NH:21][NH2:22])=[S:20]>O>[C:6]([C:5]1[C:4](=[O:15])[N:18]([NH2:17])[C:19]([SH:20])=[N:21][N:22]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 674Dimethylamine2×HCID 6416PinacoloneHCID 14798Sodium HydroxideHCID 25353Sulfur dichlorideHCID 2724189Thiocarbohydrazide

Product 1

HCID 178441961HCID 178441961, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

154.5 g (1.5 moles) of sulfur dichloride were initially introduced into a stirred flask and 100 g (1.0 mole) of pinacolone were added dropwise in the course of 2 hours at 20° - 40° C, whilst stirring and cooling slightly, HCl being released via the reflux condenser. After the reaction mixture had been stirred for a further hour at 40° C, it was added dropwise in the course of 30 - 60 minutes at 60° - 80° C, whilst cooling, to 220 ml of a 40.5% strength solution of 2 moles of dimethylamine in water. A solution of 140 g (3.5 moles) of NaOH in 300 ml of water was then added and the mixture was heated under reflux for 4 - 6 hours, dimethylamine being released as a gas via the reflux condenser and being absorbed in water. After cooling to 60° - 70° C, the pH of the mixture was adjusted to 3.0 with hydrochloric acid, whilst continuing to cool (hydrogen sulfide being released as a gas and being absorbed in sodium hydroxide solution) and elementary sulfur, which had precipitated at the same time, was filtered off. 106 g (1.0 mole) of thiocarbohydrazide were added to the clear filtrate and the mixture was reacted at pH 1 and 50° - 80° C to give 6-tert.-butyl-3-mercapto-4-amino-1,2,4-triazin-5-(4H)-one. This was very sparingly soluble in the reaction mixture and could be isolated easily by filtering off. Yield: 150 g (or 75% of theory).

Workup

  1. temperaturecooling slightly
  2. stirringAfter the reaction mixture had been stirred for a further hour at 40° C
  3. additionit was added dropwise in the course of 30 - 60 minutes at 60° - 80° C
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 4 - 6 hours
  6. custombeing absorbed in water
  7. temperatureAfter cooling to 60° - 70° C
  8. temperatureto cool (hydrogen sulfide being
  9. custombeing absorbed in sodium hydroxide solution) and elementary sulfur, which
  10. customhad precipitated at the same time
  11. filtrationwas filtered off
  12. customthe mixture was reacted at pH 1 and 50° - 80° C

Sources & evidence

ORD record
ord-c2a00017bd944ce9b93e0fb58134632f
Source dataset
uspto-grants-1978_09
Patent number
US04113767

Reaction notes

Loading…