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

HRID 478180

Reaction equation

HRID 478180 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-26fbd2868d01424191d031cd54a3fd82
Source dataset
uspto-grants-2003_11
Patent number
US06642227B2

Linked notes

Loading…