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

HRID 255404노트

반응식

HRID 255404 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 7909Methyl Isobutyl Ketone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39fe50afb8ae4397b6a9fcbd259cfcec
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04698093

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