Hydrochloric Acid → 5-Ethyl-4-(2-phenoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1153962Notes

Reaction equation

HRID 1153962 reaction equation
[OH-].[K+].[C:3]([NH:7][NH:8][C:9]([NH:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10])(=O)[CH2:4][CH3:5].Cl>O>[CH2:4]([C:3]1[N:11]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9](=[O:10])[NH:8][N:7]=1)[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13508822HCID 13508822, compound

Product 1

HCID 569735-Ethyl-4-(2-phenoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 63.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A solution of potassium hydroxide (88.4 g., 1.576 mole) in 10 liters of water is stirred and heated to 95° C.; then 1-propionyl-4-(2-phenoxyethyl)-semicarbazide (396.1 g., 1.576 mole) added and the mixture stirred at 95°-96° C. for a 40 min. period. Insolubles are collected and the filtrate stirred in an ice bath as 145 ml. (1.74 mole) of 37% hydrochloric acid is added. Stirring is continued with cooling to provide a white solid which is collected, rinsed with water and air dried to provide 233.5 g., (63.5% yield) of 5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4H)-one, m.p. 136°-139° C.

Workup

  1. customInsolubles are collected
  2. stirringthe filtrate stirred in an ice bath as 145 ml
  3. stirringStirring
  4. temperaturewith cooling
  5. customto provide a white solid which
  6. customis collected
  7. washrinsed with water and air
  8. customdried
  9. customto provide 233.5 g

Sources & evidence

ORD record
ord-69bb576ed5f64c0097cfd8e0fe8593d3
Source dataset
uspto-grants-1984_12
Patent number
US04487773

Reaction notes

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