Benzaldehyde → 3-Chloro-2-ethyl-4-(2-phenyl-1,3-dioxan-5-ylamino)-pyridine

HRID 651414

Reaktionsgleichung

Reaktionsgleichung von HRID 651414
[Cl:1][C:2]1[C:3]([NH:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])=[CH:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].NC(CO)CO.Cl[C:23]1[C:24]([CH2:30][CH3:31])=N[CH:26]=[CH:27][C:28]=1Cl.C(=O)C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:7]([CH2:8][CH3:9])=[N:6][CH:5]=[CH:4][C:3]=1[NH:10][CH:11]1[CH2:14][O:15][CH:26]([C:27]2[CH:31]=[CH:30][CH:24]=[CH:23][CH:28]=2)[O:13][CH2:12]1

Komponenten

8

Edukt 5

HCID 240BenzaldehydeHCID 68294SerinolHCID 521998p-Toluenesulfonic acid monohydrateHCID 153464515-Chloro-6-ethyl-4-(1,3-dihydroxy-2-propylamino)-pyridineHCID 217084253,4-Dichloro-2-ethylpyridine

Produkt 1

HCID 98800463-Chloro-2-ethyl-4-(2-phenyl-1,3-dioxan-5-ylamino)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2.3 g (10 mmol) of 5-chloro-6-ethyl-4-(1,3-dihydroxy-2-propylamino)-pyridine (prepared analogously to Example A from 2-amino-1,3-propanediol and 3,4-dichloro-2-ethyl-pyridine) and 5.0 g of benzaldehyde were heated with 2.1 g of p-toluenesulfonic acid hydrate in 40 ml of toluene, using a water separator, until the evolution of water had ended. Working up and purification were carried out analogously to Example A. the chromatography over silica gel (ethyl acetate) gave initially 0.6 g of trans isomer (18.8% of theory), melting point: 139-140° C., and then 2.4 g of cis isomer (75.2% of theory), melting point 119-120° C.

Aufarbeitung

  1. customWorking up and purification
  2. customthe chromatography over silica gel (ethyl acetate) gave initially 0.6 g of trans isomer (18.8% of theory), melting point: 139-140° C.

Quellen und Nachweise

ORD-Eintrag
ord-986edda2c1a54907ba8a915b5cd211e7
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281221B1

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