Hydrochloric Acid → HCID 178517825, compound

HRID 1679658Notes

Reaction equation

HRID 1679658 reaction equation
[O:1]([CH2:8][CH2:9][NH:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:12].[C:13](=[O:16])([O-])[O-].[K+].[K+].[C:19](#[N:21])C>>[O:1]([CH2:8][CH2:9][N:10]1[C:19]([Cl:12])=[N:21][C:13]([OH:16])=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 20217(2-Phenoxyethyl)hydrazine

Product 1

HCID 178517825HCID 178517825, compoundYield 43.8%

Procedure

30.4 g (0.2 mole) of 2-phenoxyethylhydrazine were dissolved in 200 ml of anhydrous acetonitrile and 7.3 g of hydrogen chloride gas were passed in at 0° C. 32 g (0.2 mole) of N-chlorocarbonyl-isocyanide-dichloride were then added dropwise to the mixture at 15°-20° C, while cooling and stirring vigorously, and after completion of the addition, 30 g of potassium carbonate were also added. The batch was next stirred for 4 hours at room temperature, in the course of which the temperature in the reaction vessel at times rose to as much as 45° C, and was then heated under reflux until no further evolution of hydrogen chloride was detectable (4-6 hours). After cooling, the residue was filtered off and washed with acetonitrile, and the total filtrate was evaporated under reduced pressure. The crystalline residue was recrystallized from a little ethanol. 21 g (43.8% of theory) of 1-(2-phenoxyethyl)-5-chloro-3-hydroxy-1,2,4-triazole of melting point 166° C were obtained. ##STR100##

Workup

  1. customwere passed in at 0° C
  2. temperaturewhile cooling
  3. additionwere also added
  4. stirringThe batch was next stirred for 4 hours at room temperature, in the course of which the temperature in the reaction vessel at times
  5. customrose to as much as 45° C
  6. temperaturewas then heated
  7. custom(4-6 hours)
  8. temperatureAfter cooling
  9. filtrationthe residue was filtered off
  10. washwashed with acetonitrile
  11. customthe total filtrate was evaporated under reduced pressure
  12. customThe crystalline residue was recrystallized from a little ethanol

Sources & evidence

ORD record
ord-c3a0a818aa454d1ba9ae32cdd076a56b
Source dataset
uspto-grants-1978_03
Patent number
US04081535

Reaction notes

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