Hydrochloric Acid → HCID 67790043, compound

HRID 274861Notes

Reaction equation

HRID 274861 reaction equation
ClC1C=CC(C(NN)=O)=CC=1.C(N=C=O)C.[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([C:22]([NH:24][NH:25][C:26]([NH:28][CH2:29][CH3:30])=[O:27])=O)=[CH:20][CH:19]=1.NNC(N)=O.Cl>O1CCCC1.[OH-].[Na+]>[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([CH:22]2[N:28]([CH2:29][CH3:30])[C:26](=[O:27])[N:25]=[N:24]2)=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5196SemicarbazideHCID 8022Ethyl isocyanateHCID 108164-ChlorobenzohydrazideHCID 13864336HCID 13864336, compound

Product 1

HCID 67790043HCID 67790043, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
10 °C

Procedure

To a suspension of 4-chlorobenzhydrazide (98.5 g, 0.05 mole) in tetrahydrofuran (100 ml) at room temperature ethylisocyanate (4.2 g, 0.05 mole) was added slowly with magnetic stirring. The reaction was slightly exothermic and the reaction mixture turned to a thick paste. Stirring was continued an additional 30 min after which the solid was collected by suction-filtration and washed with a small amount of tetrahydrofuran and dried to provide 11.6 g (96.6% yield), of 1-(4-chlorobenzoyl)-4-ethyl semicarbazide as a white solid., m.p.=242°-243° C. The above semicarbazide (10 g, 0.0414 mole) was dissolved in 1N sodium hydroxide solution (100 ml) and was refluxed with stirring for 16 hr. The solution was cooled down to about 10° C. by an ice bath and was neutralized by conc. hydrogen chloride until pH 2. The resultant white solid was collected by suction-filtration and washed with water to give 8.65 g (93.5% yield) of 3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one as a white solid. m.p.=190°-197° C. A proton NMR spectrum was consistent with the desired structure.

Workup

  1. additionwas added slowly with magnetic stirring
  2. filtrationafter which the solid was collected by suction-filtration
  3. washwashed with a small amount of tetrahydrofuran
  4. customdried
  5. customto provide 11.6 g (96.6% yield)
  6. temperaturewas refluxed
  7. stirringwith stirring for 16 hr
  8. filtrationThe resultant white solid was collected by suction-filtration
  9. washwashed with water

Sources & evidence

ORD record
ord-ecf953b60fa643bc95c033d5e2df0db9
Source dataset
uspto-grants-1995_02
Patent number
US05391561

Reaction notes

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