Dimethylformamide dimethyl acetal → 4-(3-Dimethylamino-acryloyl)-3-methyl-5-methylsulfanylthiophene-2-carbonitrile

HRID 6849

Reaction equation

HRID 6849 reaction equation
[C:1]([C:4]1[C:5]([CH3:13])=[C:6]([C:11]#[N:12])[S:7][C:8]=1[S:9][CH3:10])(=[O:3])[CH3:2].[CH3:14][N:15]([CH:17](OC)OC)[CH3:16]>C(#N)C>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:2][C:1]([C:4]1[C:5]([CH3:13])=[C:6]([C:11]#[N:12])[S:7][C:8]=1[S:9][CH3:10])=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 28201864-Acetyl-3-methyl-5-(methylthio)thiophene-2-carbonitrile

Product 1

HCID 5360484-(3-Dimethylamino-acryloyl)-3-methyl-5-methylsulfanylthiophene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-acetyl-3-methyl-5-methylsulfanyl-thiophene-2-carbonitrile (10 mmol) in acetonitrile (5 mL) was added DMF-DMA (2 mL) and the resulting mixture heated at reflux for 18 hours. The reaction was concentrated and the residue triturated with diethyl ether (20 mL). The suspension was filtered and washed with ether to afford the desired product as a yellow solid.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 18 hours
  3. concentrationThe reaction was concentrated
  4. customthe residue triturated with diethyl ether (20 mL)
  5. filtrationThe suspension was filtered
  6. washwashed with ether

Sources & evidence

ORD record
ord-415fb75af4324233a0dbe7387235e9d9
Source dataset
uspto-grants-2006_08
Patent number
US07084159B2

Linked notes

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