Methanol → 1,2-Diphenyl-3,5-pyrazolidinedione

HRID 2308146Notes

Reaction equation

[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5]CC)=O.[C:12]1([NH:18][NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO.C[O-].[Na+]>C(O)CCC>[C:20]1([N:19]2[C:1](=[O:9])[CH2:2][C:3](=[O:5])[N:18]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Three point six five (3.65) grams (22.8 mmol) of diethyl malonate and 4.00 g (21.7 mmol) of 1,2-diphenylhydrazine were dissolved in 10 ml of n-butanol, then 4.61 g (23.9 mmol) of a 28% methanol solution of sodium methoxide was added thereto, and the reaction system was heated at 100° C. for 10 hours. Subsequently, the solvent was distilled off under reduced pressure, 10 ml of water was added thereto and stirred, and then the reaction solution was filtered. An activated carbon was added to the recovered filtrate and stirred for 30 minutes. After stirring, the solution was filtered again to recover the filtrate. Four (4) ml of hydrochloric acid was added to the filtrate, and the precipitated solid was recovered by filtration. Thus, 3.76 g (yield: 60%) of 1,2-diphenyl-3,5-pyrazolidinedione was obtained.

Workup

distillationSubsequently, the solvent was distilled off under reduced pressure, 10 ml of water
additionwas added
filtrationthe reaction solution was filtered
additionAn activated carbon was added to the recovered filtrate
stirringstirred for 30 minutes
stirringAfter stirring
filtrationthe solution was filtered again
customto recover the filtrate
additionFour (4) ml of hydrochloric acid was added to the filtrate
filtrationthe precipitated solid was recovered by filtration

Sources & evidence

ORD record: ord-d985e09a4d3548eb92a196bb6bf32701
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06835474B2

Reaction notes

Loading…