Ethanol → Diethyl 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate

HRID 2291468Notes

Reaction equation

HRID 2291468 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:15][CH3:16])[C:6]([C:17]([OH:19])=[O:18])=[C:5]([C:20]([F:23])([F:22])[F:21])[N:4]=1.S(Cl)(Cl)=O.[CH2:30](O)[CH3:31]>>[F:25][C:2]([F:24])([F:1])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:15][CH3:16])[C:6]([C:17]([O:19][CH2:30][CH3:31])=[O:18])=[C:5]([C:20]([F:22])([F:21])[F:23])[N:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 140137533-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate2×

Product 1

HCID 14013779Diethyl 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate

Procedure

This material was obtained from product of Example 14 and ethanol according to the following general procedure: A 5.0 g portion of the acid product of Example 14 was refluxed with excess thionyl chloride until the reaction was completed. Excess thionyl chloride was removed in vacuo. The residual acid chloride was refluxed with an excess of appropriate alcohol (ethanol in this Example) for 2-4 hours and concentrated to give the desired product. The crude product was purified by a wash with 20% K2CO3 and isolated as a solid (20.3% yield), mp 28°-30° C.

Workup

  1. customExcess thionyl chloride was removed in vacuo
  2. temperatureThe residual acid chloride was refluxed with an excess of appropriate alcohol (ethanol in this Example) for 2-4 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-38ffde3f03dd46f9bdf049947bbb531a
Source dataset
uspto-grants-1989_01
Patent number
US04797149

Reaction notes

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