Thiophenol → Ethyl 2,6-bis(trifluoromethyl)-4-phenylthio-3-pyridinecarboxylate

HRID 542118Notes

Reaction equation

HRID 542118 reaction equation
[O-]CC.[Na+].[C:5]1([SH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:12][C:13]([F:31])([F:30])[C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18](Cl)[CH:17]=[C:16]([C:26]([F:29])([F:28])[F:27])[N:15]=1>C(O)C>[F:30][C:13]([F:12])([F:31])[C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([S:11][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:17]=[C:16]([C:26]([F:29])([F:28])[F:27])[N:15]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 2723922Sodium ethoxideHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

Product 1

HCID 13882881Ethyl 2,6-bis(trifluoromethyl)-4-phenylthio-3-pyridinecarboxylateYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1.70 g (0.025 mol) of sodium ethoxide in 100 ml ethanol was added 2.74 g (0.025 mol) of thiophenol followed by 5.3 g (0.016 mol) of product of Example 19. The reaction mixture was held at reflux for 2 days and filtered. The filtrate was poured into water and extracted into ether. The ether extract was washed with 10% NaOH, dried (MgSO4) had concentrated to give 4.14 g (63.6%) of product as a solid; mp 58°-61° C.

Workup

  1. temperatureat reflux for 2 days
  2. filtrationfiltered
  3. additionThe filtrate was poured into water
  4. extractionextracted into ether
  5. extractionThe ether extract
  6. washwas washed with 10% NaOH
  7. dry with materialdried (MgSO4)
  8. concentrationhad concentrated

Sources & evidence

ORD record
ord-a4dee23f457343a5a1c1062c1f943b4a
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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