Aniline → Ethyl 3-anilino-2-cyano-3-methylsulfanylprop-2-enoate

HRID 1914616Notes

Reaction equation

HRID 1914616 reaction equation
CS[C:3]([S:12][CH3:13])=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:10]([C:4](=[C:3]([S:12][CH3:13])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:11]

Participants

4

Reactant 2

HCID 6115AnilineHCID 2747745Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate

Product 1

HCID 4200299Ethyl 3-anilino-2-cyano-3-methylsulfanylprop-2-enoateYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3,3-bis(methylthio)-2-cyanoacrylate (20.0 g, 91.2 mmol) and aniline (9.1 mL, 100 mmol) in ethanol (200 mL) was heated under reflux for 16 hr. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=98:2→1:1) to give the title compound (21.0 g, 88%) as a white powder.

Workup

  1. temperatureunder reflux for 16 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=98:2→1:1)

Sources & evidence

ORD record
ord-0449627afbfb4dc3998f8c07148a9020
Source dataset
uspto-grants-2013_12
Patent number
US08614208B2

Reaction notes

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