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p-Bromochlorobenzene → HCID 23336425, Verbindung

HRID 903549
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 903549
C1([Mg]Br)C=CC=CC=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1.[Mg].[CH3:18][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[N:21]2[CH2:30][CH2:31][N:32]=[C:20]12>O1CCCC1.O.C(OCC)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:22]2([OH:29])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:19]([CH3:18])[C:20]3=[N:32][CH2:31][CH2:30][N:21]23)=[CH:12][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 7806p-BromochlorobenzeneHCID 731601HCID 731601, VerbindungHCID 5462224MagnesiumHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 23336425HCID 23336425, VerbindungAusbeute 26,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a phenylmagnesium bromide solution prepared from 6.9 g of p-chlorophenyl bromide, 0.88 g of magnesium and 25 ml of dry diethyl ether was added dropwise a solution of 2.42 g of 10-methyl-2,3,5,10-tetrahydroimidazo[2,1-b]quinazoline-5-one in 30 ml of dry tetrahydrofuran with stirring and ice-cooling. The mixture was heated under reflux for 2 hours and then cooled. To the mixture were added dropwise 20 ml of water and stirring was continued for a while. The resulting mixture was extracted with hot chloroform and the insoluble material was filtered off and washed with hot chloroform. The chloroform layer was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The residue was crystallized from ethanol and the crystals were further recrystallized from dimethylformamide to give 1.0 g of 5-(p-chlorophenyl)-5-hydroxy-10-methyl-2,3,5,10-tetrahydroimidazo[2,1-b]quinazoline as colorless needles, m.p. 207°-209° C. (decomp.).

Aufarbeitung

  1. temperatureice-cooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled
  5. stirringstirring
  6. extractionThe resulting mixture was extracted with hot chloroform
  7. filtrationthe insoluble material was filtered off
  8. washwashed with hot chloroform
  9. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe residue was crystallized from ethanol
  12. customthe crystals were further recrystallized from dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-fc07e85cd0424333aa0a951db1c5204b
Quelldatensatz
uspto-grants-1980_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04228167

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