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

HRID 478181

Reaction equation

HRID 478181 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-950cf2324e5e476fbb96a1f067bfa35a
Source dataset
uspto-grants-2003_11
Patent number
US06642227B2

Linked notes

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