Sulfuric Acid → HCID 178441961, compound

HRID 2285985Notes

Reaction equation

HRID 2285985 reaction equation
[C:1]([C:7]#N)(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].S(=O)(=O)(O)[OH:10].CC(=C)C.[NH2:18][NH:19][C:20]([NH:22][NH2:23])=[S:21]>C(O)(=O)C.O>[NH2:18][N:19]1[C:7](=[O:10])[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])=[N:23][N:22]=[C:20]1[SH:21]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 945273,3-Dimethyl-2-oxobutanenitrileHCID 2724189Thiocarbohydrazide

Product 1

HCID 178441961HCID 178441961, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

111 grams (1 mole) of pivaloyl cyanide were dissolved in 200 ml of glacial acetic acid and treated at 0° to +5° C. with 152 grams (1.5 moles) of 97% sulfuric acid. Within 2 hours there were led in 112.2 grams (2 moles) of isobutylene at 0° to +5° C. In connection with the one hour post reaction at 20° C. there were added at the same temperature 200 ml of glacial acetic acid and 108 grams of water. The mixture was heated at boiling in a very slow current of nitrogen for 4 hours, whereby 92 grams (82% of that employed) of isobutylene escaped and was caught in a cooling trap. The mixture was treated at 80° C. with 100 grams of water and subsequently with 92.4 grams (0.87 mole) of thiocarbohydrazide. It was stirred for a further 10 minutes at 95° to 100° C. and then cooled. By filtration there were isolated 162 grams of the triazinone (I) having a melting point of 208°-210° C. (81% of theory).

Workup

  1. customIn connection with the one hour post reaction at 20° C.
  2. temperatureThe mixture was heated
  3. customfor 4 hours
  4. customwas caught in a cooling trap
  5. temperaturecooled
  6. filtrationBy filtration there

Sources & evidence

ORD record
ord-ebcb6137816d45fe8b6cd205fba34652
Source dataset
uspto-grants-1982_04
Patent number
US04326056

Reaction notes

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