Ethyl Thioglycolate → Ethyl 4-cyano-3-(3,4-dichlorophenyl)-5-(methylsulfanyl)thiophene-2-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[C:5]([C:7](=[C:10]([S:13][CH3:14])[S:11][CH3:12])[C:8]#[N:9])=O.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])CS>CCO>[C:8]([C:7]1[C:5]([C:4]2[CH:15]=[CH:16][C:17]([Cl:18])=[C:2]([Cl:1])[CH:3]=2)=[C:12]([C:19]([O:23][CH2:24][CH3:25])=[O:22])[S:11][C:10]=1[S:13][CH3:14])#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred suspension of 2-(3,4-dichlorobenzoyl)-3,3-bis(methylsulfanyl)acrylonitrile (2.28 g, 7.16 mmol) in EtOH (31 mL) was added ethyl thioglycolate (0.864 mL, 7.88 mmol) and TEA (1.1 mL, 7.88 mmol). The reaction mixture was heated until reflux was achieved and was then allowed to cool. A solid formed. After sitting at rt overnight, the solid was filtered and washed with cold EtOH (100 mL) to give ethyl 4-cyano-3-(3,4-dichlorophenyl)-5-(methylsulfanyl)thiophene-2-carboxylate (2.38 g, 89%). 1H NMR (400 MHz, d6-DMSO) δ: 7.82 (d, 1H), 7.75 (d, 1H), 7.47 (dd, 1H), 4.14 (q, 2H), 2.82 (s, 3H) and 1.11 (t, 3H).