Water → HCID 67823296, compound

HRID 1492569Notes

Reaction equation

HRID 1492569 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]([C:21]2[CH:28]=[CH:27][C:24](C=O)=[CH:23][CH:22]=2)[CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:29]([CH2:34][CH:35]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:31][CH2:32][CH3:33])=[O:30].O.[CH2:56](Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]([C:21]2[CH:28]=[CH:27][C:24]([CH:56]=[C:34]([CH3:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=2)[CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoateHCID 53839507HCID 53839507, compound

Product 1

HCID 67823296HCID 67823296, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The solution of 220 mg of 4-[3-(4-chlorobenzenesulfonamido)-1-(3-pyridyl)-2-propyl]benzaldehyde and 420 mg of (carboethoxyethylidene)triphenylphosphorane in 20 ml of chloroform in solution was stirred under heating for five hours. To the reaction mixture was added water, followed by separation of the organic phase, which was then extracted with methylene chloride. After washing in saturated aqueous sodium chloride solution, the product was then dried over magnesium sulfate, followed by evaporation of the solvent. The residue obtained was subjected to preparative TLC on silica gel, which was developed with methylene chloride three times, to obtain 186 mg of ethyl 4-[3-(4-chlorobenzenesulfonamido)-1-(3-pyridyl)-2-propyl]-α-methylcinnamate. The spectrometric data thereof supports the structure of [46] as follows.

Workup

  1. temperatureunder heating for five hours
  2. customfollowed by separation of the organic phase, which
  3. extractionwas then extracted with methylene chloride
  4. washAfter washing in saturated aqueous sodium chloride solution
  5. dry with materialthe product was then dried over magnesium sulfate
  6. customfollowed by evaporation of the solvent
  7. customThe residue obtained

Sources & evidence

ORD record
ord-02b113a385b347a5a686e4060ce94492
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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