Hydrochloric Acid → 4-(4-Acetylphenyl)-1,2,4-triazolidine-3,5-dione

HRID 1746260Notes

Reaction equation

HRID 1746260 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][NH:14][C:15]([O:17]CC)=O)=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl.O1CCOCC1>CO>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:11](=[O:12])[NH:13][NH:14][C:15]2=[O:17])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2208922Ethyl 2-(4-acetylphenylcarbamoyl)hydrazinecarboxylate

Product 1

HCID 533076914-(4-Acetylphenyl)-1,2,4-triazolidine-3,5-dioneYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To ethyl 2-(4-acetylphenylcarbamoyl)hydrazinecarboxylate (I-4a: 354 mg, 1.335 mmol) in MeOH (10 mL) was added K2CO3 (553 mg, 4.00 mmol). The mixture was stirred at 55° C. for 2 hours, cooled to room temperature, and then HCl 4N in dioxane (1.668 mL, 6.67 mmol) was added. The precipitate was filtered, and the filtrate was concentrated in vacuo. The resulting solid was triturated in CH2Cl2, filtered and dried giving 4-(4-acetylphenyl)-1,2,4-triazolidine-3,5-dione (I-4b: 125 mg, 43%) as a light yellow solid. LC-MS (M+1) 220.2, t=0.78 minute. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.60 (s, 3 H) 7.68 (d, J=8.84 Hz, 2 H) 8.05 (d, J=8.59 Hz, 2 H) 10.65 (s, 2 H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe resulting solid was triturated in CH2Cl2
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-2503cadea86948c5b423e519923c75b3
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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