Methyl Ethyl Ketone → HCID 15917390, Verbindung

HRID 1758141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758141
Cl[C:2]1[N:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])=[N:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[Cl:8][C:5]1[CH:4]=[N:3][C:2]([O:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][N:14]=2)=[N:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 5906412,5-DichloropyrimidineHCID 15917385HCID 15917385, Verbindung

Produkt 1

HCID 15917390HCID 15917390, VerbindungAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

With stirring, 1.80 grams (0.012 mole) of 2,5-dichloropyrimidine was added to a mixture of 2.0 grams (0.009 mole) 2-(5-chloropyridin-2-yloxy)phenol, 1.5 grams potassium carbonate, and 40 ml of methyl ethyl ketone. After the addition, the mixture was heated at reflux overnight and then poured into excess H2O. After extracting with 200 ml of ethyl ether, the extract was washed with saturated NaHCO3, H2O, brine, dried (MgSO4), filtered, and evaporated to yield a yellow solid which was recrystallized from 1-chlorobutane to give 2.3 grams of product, m.p. 108°-111°; ir (Nujol): 6.35, 6.50 (C=N), 13.20 microns; NMR (CDCl3): δ6.75 (d, 1H, pyridine ring proton), 7.35 (s, 4H, ArH), 7.65 (AB quartet, 1H, pyridine ring proton), 8.10 (d, 1H, pyridine ring proton), 8.55 (s, 2H, pyrimidine ring protons).

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux overnight
  4. extractionAfter extracting with 200 ml of ethyl ether
  5. washthe extract was washed with saturated NaHCO3, H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto yield a yellow solid which
  10. customwas recrystallized from 1-chlorobutane

Quellen und Nachweise

ORD-Eintrag
ord-3c64b94e12174b92bf7918d0de5db1de
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04371736

Notizen zur Reaktion

Wird geladen…