Benzaldehyde → 2-(Benzenesulfonyl)-3-[4-(2-phenylethenyl)phenyl]prop-2-enenitrile

HRID 1414171Notes

Reaction equation

HRID 1414171 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([CH:7]=[C:8]([C:18]#[N:19])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:3][CH:2]=1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)C>CN(C)C=O>[C:1]1([CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:2]=[CH:3][C:4]([CH:7]=[C:8]([C:18]#[N:19])[S:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 702EthanolHCID 5067622HCID 5067622, compound

Product 1

HCID 542956762-(Benzenesulfonyl)-3-[4-(2-phenylethenyl)phenyl]prop-2-enenitrileYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

12.48 g (20 mmole) of the triphenylphosphonium bromide of Example 1 c) were dissolved in 200 ml of absolute dimethylformamide at 70° C, by stirring and under an atmosphere of nitrogen. After the mixture had cooled to 30° to 35° C, 2.24 g (20 mmole) of potassium-tert. butylate were introduced and the whole was stirred again for 5 minutes. The solution of 2.12 g (20 mmole) of benzaldehyde in 20 ml of absolute dimethylformamide was added dropwise within 10 minutes to the violet solution and the whole was further heated for 4 hours to 100° C under an atmosphere of nitrogen. After cooling, the potassium bromide separated was filtered off with suction and the dimethylformamide was eliminated by destillation on a rotary vaporator and under a vacuum produced by a water jet. The residue was combined with 200 ml of hot ethanol. After cooling, 4.65 g of weakly yellow crystals of 1-(stilbene-4-yl)-2-cyano-2-phenylsulfonylethylene having a melting point of 179° to 183° C (corresponding to a yield of 63% of the theory), were obtained. ##STR17##

Workup

  1. temperatureAfter the mixture had cooled to 30° to 35° C
  2. stirringthe whole was stirred again for 5 minutes
  3. temperaturethe whole was further heated for 4 hours to 100° C under an atmosphere of nitrogen
  4. temperatureAfter cooling
  5. customthe potassium bromide separated
  6. filtrationwas filtered off with suction
  7. customproduced by a water jet
  8. temperatureAfter cooling

Sources & evidence

ORD record
ord-e5b9175cc0904ed59b4a2a54f213927c
Source dataset
uspto-grants-1977_01
Patent number
US04001221

Reaction notes

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