Hydrochloric Acid → 3H-1,2,4-Triazol-3-one, 5-(4-chlorophenyl)-4-ethyl-2,4-dihydro-

HRID 1708907Notes

Reaction equation

HRID 1708907 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])=O)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]2[N:12]([CH2:13][CH3:14])[C:10](=[O:11])[NH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13864336HCID 13864336, compound

Product 1

HCID 357933H-1,2,4-Triazol-3-one, 5-(4-chlorophenyl)-4-ethyl-2,4-dihydro-

Procedure

1-(4-chlorobenzoyl)-4-ethylsemicarbazide (23.7 g, 9.81×10-2 mole) and 1 molar aqueous NaOH (118 ml, 1.18×10-1 mole) were stirred and warmed to reflux. After refluxing 23 hours, heating was discontinued and the reaction was acidified by the dropwise addition of 1 molar aqueous hydrochloric acid (130 ml, 1.30×10-1 mole). A colorless solid formed as the reaction was acidified and, after cooling in an ice bath, this was collected by filtration. Crystallization from isopropanol gave colorless spars: 18.2 g (83%), mp 188°-189°.

Workup

  1. temperaturewarmed to reflux
  2. temperatureAfter refluxing 23 hours
  3. temperatureheating
  4. customA colorless solid formed as the reaction
  5. temperatureafter cooling in an ice bath
  6. filtrationthis was collected by filtration
  7. customCrystallization from isopropanol
  8. customgave colorless spars

Sources & evidence

ORD record
ord-05f463c5982041c9b099d692c11048e4
Source dataset
uspto-grants-1990_08
Patent number
US04946856

Reaction notes

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