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(Ethylsulfonyl)ethene → 2-(2'-Ethylsulfonylethyl)-4-cyano-5,6-diphenyl-3-(2H)-pyridazinone

HRID 463970
Notes
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Reaction equation

HRID 463970 reaction equation
[C:1]([C:3]1[C:4](=[O:21])[NH:5][N:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:2].[CH2:22]([S:24]([CH:27]=[CH2:28])(=[O:26])=[O:25])[CH3:23]>N1C=CC=CC=1>[CH2:22]([S:24]([CH2:27][CH2:28][N:5]1[C:4](=[O:21])[C:3]([C:1]#[N:2])=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:6]1)(=[O:26])=[O:25])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 74680(Ethylsulfonyl)etheneHCID 957574-Pyridazinecarbonitrile, 2,3-dihydro-3-oxo-5,6-diphenyl-

Product 1

HCID 135335082-(2'-Ethylsulfonylethyl)-4-cyano-5,6-diphenyl-3-(2H)-pyridazinoneYield 72.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.0 grams (0.0175 mole) of the product of Example 1 was reacted with 2.1 grams of ethyl-vinyl sulfone in 60 mls of pyridine. This solution was heated on a steam bath for 2 hours, cooled and the solvent distilled at reduced pressure. The residual oil was taken up in ethyl alcohol. 5.0 grams (72% yield) of a solid precipitated and was filtered, washed with petroleum ether and air dried. The infrared spectrum showed the nitrile band at 4.5μ, the carbonyl band at 6.0μ, the SO2 band at 8.7μ.

Workup

  1. temperatureThis solution was heated on a steam bath for 2 hours
  2. temperaturecooled
  3. distillationthe solvent distilled at reduced pressure

Sources & evidence

ORD record
ord-b64e44dccc5545a2ae730aec6463de69
Source dataset
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04545810

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes