Ethanethiol → Ethyl 4-ethylthio-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate

HRID 1649653Notes

Reaction equation

HRID 1649653 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7](Cl)[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:27]([SH:29])[CH3:28]>C(C(C)=O)C(C)C>[CH2:27]([S:29][C:7]1[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=[C:3]([C:2]([F:20])([F:19])[F:1])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:28]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

Product 1

HCID 13882883Ethyl 4-ethylthio-2,6-bis(trifluoromethyl)-3-pyridinecarboxylateYield 69.8%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.0 g (0.009 mol) of product of Example 9, 1.55 g (0.011 mol) of K2CO3 and 3.5 ml (0.047 mol) of ethanethiol in 15 ml of methyl isobutyl ketone was stirred at reflux for 60 hours. The reaction mixture was concentrated. The residue was taken up in ether, washed with 10% NaOH and water, dried (MgSO4) and concentrated in vacuo to 2.98 g of dark oil which was purified by HPLC using 5% ethyl acetate/cyclohexane as eluting solvent affording 2.18 g (69.8%) of product as a tan solid; mp 36°-37.5° C.

Workup

  1. temperatureat reflux for 60 hours
  2. concentrationThe reaction mixture was concentrated
  3. washwashed with 10% NaOH and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo to 2.98 g of dark oil which
  6. customwas purified by HPLC
  7. washas eluting solvent

Sources & evidence

ORD record
ord-720b829c47874d0a824ff9ba311da971
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

Loading…