Methyl iodide → HCID 627529, compound

HRID 1192254Notes

Reaction equation

HRID 1192254 reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].[C:12](=O)([O-])[O-].[K+].[K+].[C:18](=[S:20])=[S:19].Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].IC>>[C:4]([C:3]1[C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:19][C:18]=1[S:20][CH3:12])#[N:5]

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 64799Benzoylacetonitrile

Product 1

HCID 627529HCID 627529, compound

Procedure

3-oxo-3-phenylpropanenitrile (0.725 g, 5.0 mmol) was added to a suspension of potassium carbonate (1.98 g, 15.0 mmol) in N,N-dimethylformide (4.5 mL) and allowed to stir at ambient temperature. After 10 minutes, carbon disulfide (0.57 g, 7.5 mmol) was added in one portion and the resulting mixture stirred at ambient temperature for an additional 10 minutes then a solution of ethyl 2-chloroacetate (0.61 g, 5.0 mmol) in N,N-dimethylformide (5.0 mL) was added. After 1 hour, a solution of iodomethane (0.78 g, 5.0 mmol) in N,N-dimethylformide (2 mL) was added in a dropwise fashion then, after 30 minutes, the mixture was poured onto water and the resulting mixture was stirred for 16 hours to afford a suspension of the title product. The resulting precipitate was collected by filtration, washed with water (10 mL) and dried in vacuo overnight. The title product was obtained as a white solid (0.86 g, 56% yield). MS m/z: 326.89, 328.89 [M+Na]+.

Workup

  1. stirringthe resulting mixture stirred at ambient 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 for 16 hours
  6. customto afford

Sources & evidence

ORD record
ord-ea37e448a2b44388b21809c6f605cf63
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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