Acetic Acid → 2-[(4-Methylphenyl)sulfonyl]-3-[4-(3-methylthio(2-thienyl))phenyl]prop-2-enenitrile

HRID 1865127Notes

Reaction equation

HRID 1865127 reaction equation
[CH3:1][S:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([S:22]([CH2:25][C:26]#[N:27])(=[O:24])=[O:23])=[CH:18][CH:17]=1.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:28][C:16]1[CH:17]=[CH:18][C:19]([S:22]([C:25](=[CH:12][C:11]2[CH:14]=[CH:15][C:8]([C:4]3[S:5][CH:6]=[CH:7][C:3]=3[S:2][CH3:1])=[CH:9][CH:10]=2)[C:26]#[N:27])(=[O:24])=[O:23])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 79776TosylacetonitrileHCID 579753594-(3-Methylthio-2-thienyl)benzaldehyde

Product 1

HCID 690201762-[(4-Methylphenyl)sulfonyl]-3-[4-(3-methylthio(2-thienyl))phenyl]prop-2-enenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirring solution of 4-(3-methylthio-2-thienyl)benzaldehyde (1.0 mmol, prepared directly above) and p-toluenesulphonylacetonitrile (1.0 mmol) in toluene, add piperidine (0.05 mmol) and acetic acid (0.3 mmol). Heat the reaction mixture to reflux for 2 hours while using a Dean-Stark trap, remove the heat and concentrate the reaction in vacuo. The crude material can be carried on to the next step without further purification.

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureto reflux for 2 hours
  3. customremove the
  4. temperatureheat
  5. concentrationconcentrate
  6. customthe reaction in vacuo
  7. customThe crude material can be carried on to the next step without further purification

Sources & evidence

ORD record
ord-e678d31c3812410c82607739188924b7
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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