Pyridine → N-(4-Chlorophenyl)-3-oxo-2-phenylpyrazolidine-1-carbothioamide

HRID 1388332Notes

Reaction equation

HRID 1388332 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[S:22])=[CH:16][CH:15]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:8]2[CH2:9][CH2:10][C:11](=[O:12])[N:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[S:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 164804-Chlorophenyl isothiocyanateHCID 3195992-Phenylpyrazolidin-3-one

Product 1

HCID 13272160N-(4-Chlorophenyl)-3-oxo-2-phenylpyrazolidine-1-carbothioamideYield 90.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.11 grams (0.013 mole) of 2-phenyl-3-pyrazolidinone, 2.21 grams (0.013 mole) of 4-chlorophenyl isothiocyanate and 0.5 ml of pyridine in 15 ml of toluene was heated at reflux for 9 hours. The reaction mixture was allowed to cool to room temperature forming a crystalline precipitate. The crystalline precipitate was collected by filtration to yield 3.92 grams of 1-(4-chlorophenylthiocarbamoyl)-2-phenyl-3-pyrazolidinone (mp 136°-139° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 9 hours
  3. customforming a crystalline precipitate
  4. filtrationThe crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-67cbdd4de66e40d5a0fe4f7fba759901
Source dataset
uspto-grants-1984_02
Patent number
US04431659

Reaction notes

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