Methyl iodide → alpha-Methyl-p-(2-thenoyl)hydratroponitrile
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
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
- stirringupon completion, the whole is stirred overnight
- additionThe reaction mixture is poured onto water
- extractionthe product is extracted three times with 200 parts of benzene
- washThe combined extracts are washed five times with water
- customdried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-e64ddb21d5a042ecab1d1034321e9cfc
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04060528
Reaction notes
Loading…