Ethyl Thioglycolate → Ethyl 4-cyano-3-(3,4-dichlorophenyl)-5-(methylsulfanyl)thiophene-2-carboxylate

HRID 572623Notes

Reaction equation

HRID 572623 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

HCID 12185Ethyl ThioglycolateHCID 12451263HCID 12451263, compound

Product 1

HCID 68629308Ethyl 4-cyano-3-(3,4-dichlorophenyl)-5-(methylsulfanyl)thiophene-2-carboxylateYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureuntil reflux
  3. temperatureto cool
  4. customA solid formed
  5. filtrationthe solid was filtered
  6. washwashed with cold EtOH (100 mL)

Sources & evidence

ORD record
ord-4ace4948132042a5a5c1c2ec1344665d
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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