Methyl iodide → alpha-Methyl-p-(2-thenoyl)hydratroponitrile

HRID 258907Notes

Reaction equation

HRID 258907 reaction equation
[H-].[Na+].[C:3]1([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#N)=[CH:12][CH:11]=2)=[O:9])[S:7][CH:6]=[CH:5][CH:4]=1.[CH3:19]I.C[N:22]([CH3:31])P(N(C)C)(N(C)C)=O>>[CH3:19][C:16]([C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[C:3]2[S:7][CH:6]=[CH:5][CH:4]=2)=[CH:11][CH:12]=1)([CH3:17])[C:31]#[N:22]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 122329742-[p-(2-Thenoyl)phenyl]acetonitrile

Product 1

HCID 21391796alpha-Methyl-p-(2-thenoyl)hydratroponitrile

Procedure

To a stirred mixture of 5.5 parts of sodium hydride dispersion 78% in 150 parts of hexamethylphosphoramide are added dropwise 14 parts of 2-[p-(2-thenoyl)phenyl] acetonitrile over a period of 30 minutes at a temperature of 15° C. Upon completion, stirring is continued for 3 hours at room temperature. Then there are added dropwise 34 parts of methyl iodide (strong exothermic reaction) and upon completion, the whole is stirred overnight. The reaction mixture is poured onto water and the product is extracted three times with 200 parts of benzene. The combined extracts are washed five times with water, dried, filtered and evaporated, yielding α-methyl-p-(2-thenoyl)hydratroponitrile as a residue.

Workup

  1. stirringupon completion, the whole is stirred overnight
  2. additionThe reaction mixture is poured onto water
  3. extractionthe product is extracted three times with 200 parts of benzene
  4. washThe combined extracts are washed five times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4467db2fec654309a1292642c22712dd
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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