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

HRID 255404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255404
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 13882883Ethyl 4-ethylthio-2,6-bis(trifluoromethyl)-3-pyridinecarboxylateAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

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. Anal. Calc'd. for C12H11F6N1O2S1 : C, 41.50; H, 3.19; N, 4.03. Found: C, 41.45; H, 3.22; N, 4.01.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-39fe50afb8ae4397b6a9fcbd259cfcec
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04698093

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