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Hydrochloric Acid → 9-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-phenyl-6H-pyrimido[2,1-a]isoindol-5-ium hydroxide

HRID 256697
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 256697
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[N:11][CH3:12])=[CH:4][CH:3]=1.Cl.[OH-].[Na+].[C:16](=[C:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19](Cl)=[O:20])=[O:17].N12CCCC1=NCCC2>C1(C)C=CC=CC=1.O>[OH-:17].[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N+:7]3[C:16]([OH:17])=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:19](=[O:20])[N:11]([CH3:12])[C:8]=32)=[CH:4][CH:3]=1
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Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 107737343-Oxo-2-phenylprop-2-enoyl chlorideHCID 1356242226-Chloro-1-(methylimino)isoindoline

Produkt 1

HCID 178479890
9-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-phenyl-6H-pyrimido[2,1-a]isoindol-5-ium hydroxide
Ausbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of 5.42 g of 6-chloro-1-(methylimino)isoindoline (prepared from the hydrochloride by treatment with 1.5 equivalents of 2N sodium hydroxide solution) and 120 ml of toluene was treated dropwise under argon at 0-50 within 10 minutes with 5.96 g of α-carbonyl-phenylacetyl chloride. The mixture was stirred for 30 minutes, 4.47 g of 1,5-diazabicyclo[4.3.0]non-5-ene in 30 ml of toluene were subsequently added dropwise thereto, the mixture was stirred at 0-50 for a further 90 minutes, then treated with 50 ml of water and the separated crystals were filtered off under suction and washed with 35 ml of methylene chloride and, after drying, there was obtained 3.66 g of 9-chloro1,2-dihydro-4-hydroxy-1-methyl-2-oxo -3-phenyl-6H-pyrimido[2,1-a]isoindole-5-ium hydroxide (internal salt) with a m.p. of 245° (decomposition). This product was recrystallized from N,N-dimethylformamide and then had a m.p. of 288°.

Aufarbeitung

  1. stirringthe mixture was stirred at 0-50 for a further 90 minutes
  2. filtrationthe separated crystals were filtered off under suction
  3. washwashed with 35 ml of methylene chloride
  4. customafter drying

Quellen und Nachweise

ORD-Eintrag
ord-6668cfc4fe5f40478b199852ca427141
Quelldatensatz
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05258387

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