4-Chlorophenyl isothiocyanate → N,2-Bis(4-chlorophenyl)-3-oxopyrazolidine-1-carbothioamide

HRID 1388333Notes

Reaction equation

HRID 1388333 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[S:25])=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([N:9]2[CH2:10][CH2:11][C:12](=[O:13])[N:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[S:25])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 164804-Chlorophenyl isothiocyanateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 132721582-(4-Chlorophenyl)pyrazolidin-3-one

Product 1

HCID 13272159N,2-Bis(4-chlorophenyl)-3-oxopyrazolidine-1-carbothioamideYield 47.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

Under a dry argon atmosphere a solution of 1.6 grams (0.008 mole) of 2-(4-chlorophenyl)-3-pyrazolidinone in 13 ml of tetrahydrofuran was added dropwise to a stirred mixture of 0.4 gram (0.009 mole) of sodium hydride (55% oil suspension, oil removed by washing with hexane) in 8 ml of dry tetrahydrofuran while at room temperature. After complete addition, the reaction mixture was heated at 50° C. until gas evolution ceased, then cooled to room temperature. A solution of 1.4 grams (0.008 mole) of 4-chlorophenyl isothiocyanate in 8 ml of tetrahydrofuran was added to the reaction mixture and the resultant mixture stirred at room temperature for 14 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture and the total extracted with ethyl acetate. The organic extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and filtered. The solvent was removed by distillation under reduced pressure leaving a solid residue. The solid was purified by recrystallization from ethanol to afford 1.4 grams of 1-(4-chlorophenyl)thiocarbamoyl-2-(4-chlorophenyl)-3-pyrazolidinone (mp 121°-124° C.).

Workup

  1. additionAfter complete addition
  2. temperaturecooled to room temperature
  3. extractionthe total extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed by distillation under reduced pressure
  9. customleaving a solid residue
  10. customThe solid was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-c473bffe8a5d47dea8ee99d7547d8b59
Source dataset
uspto-grants-1984_02
Patent number
US04431659

Reaction notes

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