Methyl iodide → 4-Acetyl-3-methyl-5-(methylthio)thiophene-2-carbonitrile

HRID 6848

Reaction equation

HRID 6848 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=O)[CH3:5].[C:8]([O-])([O-])=O.[K+].[K+].[C:14](=[S:16])=[S:15].Cl[CH2:18][C:19]#[N:20].CI>CN(C=O)C.O>[C:2]([C:3]1[C:4]([CH3:5])=[C:18]([C:19]#[N:20])[S:15][C:14]=1[S:16][CH3:8])(=[O:7])[CH3:1]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 28201864-Acetyl-3-methyl-5-(methylthio)thiophene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a slurry of 2,4-pentanedione (20 mmol) and K2CO3 (3 equivalents, 60 mmol) in DMF (10 mL) was added CS2 (1.2 equivalents, 24 mmol) and the resulting mixture stirred for 10 minutes. The mixture was cooled to 0° C. then chloroacetonitrile (1.0 equivalent, 20 mmol) was added and the reaction stirred 1 hour then warmed to room temperature and stirred for an additional 2 hours. The reaction mixture was again cooled to 0° C. and methyl iodide (1.05 equivalents, 22 mmol) was added slowly. The resulting mixture was warmed to room temperature. After 12 hours, water was added and the resulting suspension was stirred overnight. The desired product was isolated by filtration after washing with water.

Workup

  1. stirringthe reaction stirred 1 hour
  2. temperaturethen warmed to room temperature
  3. stirringstirred for an additional 2 hours
  4. temperatureThe reaction mixture was again cooled to 0° C.
  5. temperatureThe resulting mixture was warmed to room temperature
  6. waitAfter 12 hours
  7. stirringthe resulting suspension was stirred overnight

Sources & evidence

ORD record
ord-fab1cf601eeb4f96bf3c58d1ce626549
Source dataset
uspto-grants-2006_08
Patent number
US07084159B2

Linked notes

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