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

HRID 478178

Reaction equation

HRID 478178 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]#[N:11])=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].[C:19](=[S:21])=[S:20].Cl[CH2:23][C:24](=[O:26])[CH3:25].CI>CN(C=O)C>[C:24]([C:25]1[S:20][C:19]([S:21][CH3:13])=[C:9]([C:10]#[N:11])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:26])[CH3:23]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 5225133-(4-Methylphenyl)-3-oxopropanenitrile

Product 1

HCID 220190295-Acetyl-2-methylsulfanyl-4-(4-methyl-phenyl)-thiophene-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3-(4-Methyl-phenyl)-3-oxo-propionitrile (5 mmol) was added to a suspension of K2CO3 (3 equivalents, 15 mmol) in DMF (4.5 mL) and allowed to stir at room temperature. After 10 minutes, CS2 (1.25 equivalents, 7.5 mmol) was added in one portion and the resulting mixture stirred at room temperature for an additional 10 minutes. A solution of 1-chloro-propan-2-one (1.0 equivalent, 5 mmol) in DMF (5 mL) was added. After 1 hour, a solution of MeI (1.1 equivalents, 5.5 mmol) in DMF (2 mL) was added in a dropwise fashion. After 30 minutes, the mixture was poured onto water and the resulting mixture was stirred vigorously for 12-16 hours to afford a suspension of the desired product. The crude product was isolated by filtration.

Workup

  1. stirringthe resulting mixture stirred at room temperature for an additional 10 minutes
  2. waitAfter 1 hour
  3. waitAfter 30 minutes
  4. additionthe mixture was poured onto water
  5. stirringthe resulting mixture was stirred vigorously for 12-16 hours
  6. customto afford

Sources & evidence

ORD record
ord-44f98405d5d643d3857ebadae006d0e6
Source dataset
uspto-grants-2003_11
Patent number
US06642227B2

Linked notes

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