Reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[C:12](OCC)(=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>[O-]CC.[Na+]>[C:10]([CH:9]([C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1)[C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
By following the procedures outlined in Examples 1 and 3, p-methylthiophenylacetonitrile is reacted with diethyl oxalate in alcoholic sodium ethoxide solution to give ethyl 3-cyano-3-(p-methylthiophenyl)-pyruvate. This compound is similarly reacted with p-methylthiophenylacetonitrile which results in the formation of 2,5-di-(p-methylthiophenyl)-3,4-dioxoadiponitrile. The latter is refluxed with water, acetic acid and sulfuric acid to obtain 4,4'-dimethylthiopulvinic acid which is treated with acetic anhydride to give the corresponding acid lactone.
Sources & evidence
- ORD record
- ord-eccaed0f530e47578448a5e2ee8dcf84
- Source dataset
- uspto-grants-1976_03
- Patent number
- US03944571
Linked notes
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