Methyl iodide → Thiophene-3-carbonitrile, 5-acetyl-4-(4-chlorophenyl)-2-methylthio-

HRID 6846

Reaction equation

HRID 6846 reaction equation
[Cl: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]([Cl:1])=[CH:3][CH:4]=1)(=[O:26])[CH3:23]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 1383084-Chlorobenzoylacetonitrile

Product 1

HCID 627943Thiophene-3-carbonitrile, 5-acetyl-4-(4-chlorophenyl)-2-methylthio-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3-(4-Chloro-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 then 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 then, 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-a8501356412b4821bc14f268d1131b78
Source dataset
uspto-grants-2006_08
Patent number
US07084159B2

Linked notes

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