Hydrochloric Acid → HCID 15220959, compound

HRID 1608963Notes

Reaction equation

HRID 1608963 reaction equation
[C:1]1([CH:7]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][NH:9][C:8]2=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:22]1[S:23][C:24]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:25]=2[N:26]=1.Cl>C1(C)C=CC=CC=1>[Cl:31][C:29]1[CH:28]=[CH:27][C:25]2[N:26]=[C:22]([N:10]3[CH:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:8](=[O:18])[NH:9]3)[S:23][C:24]=2[CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 771762,6-DichlorobenzothiazoleHCID 2704924,5-diphenyltetrahydro-3h-pyrazol-3-one

Product 1

HCID 15220959HCID 15220959, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

The reaction was conducted under a dry nitrogen atmosphere. A suspension of 4,5-diphenyl-3-pyrazolidinone (1.19 g, 5.00 mmol) in 35 mL toluene was treated with 0.40 g NaH (60% in mineral oil; hydride content 0.24 g, 10.0 mmol, 2.00 eq.), and the mixture stirred at 45° C. for 2 hours. 2,6-Dichlorobenzothiazole (1.02 g, 5.00 mmol, 1.00 eq.) was added and stirring continued at 80° C. for 20 hours. After cooling, the reaction mixture was poured onto 30 mL ice-cooled 0.5 N HCl, extracted with EtOAc, and the separated organic phase washed twice with brine, dried over Na2SO4, and the solvent evaporated in vacuo. The residue was recrystallized from Et2O:hexane to provide 1.46 g (72%) light tan crystals: mp 170.5°-2.5° C.

Workup

  1. stirringstirring
  2. waitcontinued at 80° C. for 20 hours
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc
  5. washthe separated organic phase washed twice with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent evaporated in vacuo
  8. customThe residue was recrystallized from Et2O
  9. customhexane to provide 1.46 g (72%) light tan crystals

Sources & evidence

ORD record
ord-83d6f5eeb98d48cd9e90a5b19f6efa1d
Source dataset
uspto-grants-1995_03
Patent number
US05399565

Reaction notes

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