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

HRID 542119ノート

反応式

HRID 542119 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

A mixture of 3.0 g (0.009 mol) of product of Example 19, 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.

後処理

  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

出典と根拠

ORDレコード
ord-30d4e0ee01f34c6a9a6d20f26f3fddfa
出典データセット
uspto-grants-1987_04
特許番号
US04655816

反応ノート

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