2-Benzoyl-3,3-di(methylthio)acrylonitrile → HCID 10172530, compound

HRID 2183744Notes

Reaction equation

HRID 2183744 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][N:4]=1)[NH2:2].[C:13]([C:21]([C:27]#[N:28])=[C:22](SC)[S:23][CH3:24])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C.O>[CH3:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([N:1]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:21]([C:27]#[N:28])[C:22]([S:23][CH3:24])=[N:2]2)=[N:4][CH:5]=1)(=[O:10])=[O:11]

Participants

5

Reactant 2

HCID 28190822-Benzoyl-3,3-di(methylthio)acrylonitrileHCID 99642932-Hydrazino-5-(methanesulfonyl)-pyridine

Product 1

HCID 10172530HCID 10172530, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of the 2-hydrazino-5-methylsulfonyl pyridine (180 mg, 0.81 mmol) and 1-benzoyl-2,2-bis(methylthio)-1-cyano ethene (201 mg, 0.81 mmol) in anhydrous ethanol was refluxed overnight. The resulting solution was cooled to room temperature, diluted with water (25 ml) and extracted with ethyl acetate (2×25 ml). The ethyl acetate layer was dried with sodium sulfate and concentrated to give crude product. Chromatography of the mixture led to the isolation of the desired product (26 mg, 9%) in the form of a white solid.

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with ethyl acetate (2×25 ml)
  3. dry with materialThe ethyl acetate layer was dried with sodium sulfate
  4. concentrationconcentrated
  5. customto give crude product

Sources & evidence

ORD record
ord-0e9dbda1019f4baaab77442f512e6a04
Source dataset
uspto-grants-2005_05
Patent number
US06900230B2

Reaction notes

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