Hydrochloric Acid → Diethyl 2-(difluoromethyl)-4-ethyl-6-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 1111072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1111072
[F:1][C:2]([F:26])([F:25])[C:3]1[NH:4][C:5]([C:21](F)([F:23])[F:22])=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]([CH2:14][CH3:15])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].N12CCCNC1C=CCCC2.Cl>O1CCCC1>[F:23][CH:21]([F:22])[C:5]1[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]([CH2:14][CH3:15])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:3]([C:2]([F:26])([F:1])[F:25])[N:4]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 139576211,4-Dihydro-2,6-bis(trifluoromethyl)-4-ethylpyridine-3,5-dicarboxylic acid diethyl esterHCID 150726561,2,3,4,6,7,8,10A-octahydropyrimido[1,2-a]azepine

Produkt 1

HCID 13957657Diethyl 2-(difluoromethyl)-4-ethyl-6-(trifluoromethyl)-3,5-pyridinedicarboxylateAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1558 g (4.00 moles) of diethyl 2,6-bis(trifluoromethyl)-l,4-dihydro-4-ethyl-3,5-pyridinedicarboxylate, 628 g (4.0 moles) of 1,8-diazabicyclo-[5.4.0]-undec-5-ene (DBU), and 500 ml of tetrahydrofuran is held at reflux for 19 hours, cooled and poured into a mixture of 2 kg of ice and 250 ml of concentrated hydrochloric acid. The organic layer is separated and the aqueous layer extracted with 500 ml of CH2Cl2 twice. The combined organic materials are dried (MgSO4) and concentrated. The residue is kugelrohr distilled at 1 torr (pot temperature of 150°-160 ° C.) to give 1158 g (78.5%) of desired product, nD25 1.4458.

Aufarbeitung

  1. temperatureat reflux for 19 hours
  2. temperaturecooled
  3. customThe organic layer is separated
  4. extractionthe aqueous layer extracted with 500 ml of CH2Cl2 twice
  5. dry with materialThe combined organic materials are dried (MgSO4)
  6. concentrationconcentrated
  7. distillationThe residue is kugelrohr distilled at 1 torr (pot temperature of 150°-160 ° C.)

Quellen und Nachweise

ORD-Eintrag
ord-db5cc8ae637640d4bc5e52d5c8cbf950
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04978384

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