Diethyl benzylphosphonate → 5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-4-styryl-1H-pyrazole

HRID 47608

Reaction equation

HRID 47608 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=[C:12]([CH3:21])[C:11]=2[CH:22]=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:24](P(=O)(OCC)OCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=[C:12]([CH3:21])[C:11]=2[CH:22]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 227474725-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 695160655-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-4-styryl-1H-pyrazoleYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing 164 mg of 5-(3,5-dichloro-phenylsulphanyl)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, 103 mg of diethyl benzylphosphonate and 27 mg of sodium hydride (60% in mineral oil) in 5 ml of anhydrous tetrahydrofuran was stirred under nitrogen at rt for 16 h. The solvent was evaporated and the residue was purified by flash chromatography on silica gel using ethyl acetate/petroleum spirit 40°-60° C. (1:10) for the elution to give 162 mg of 5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-4-styryl-1H-pyrazole as a pale yellow solid. Mass spectrum (EI) m/z 436 [M]+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography on silica gel
  3. customethyl acetate/petroleum spirit 40°-60° C. (1:10)
  4. washfor the elution

Sources & evidence

ORD record
ord-bc0e1c67252a4e75a6d50b2b57340c79
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Linked notes

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