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Carbon Disulfide → 4-[(4-CHLOROPHENYL)METHYL]-2,3,6,7-TETRAHYDRO-2-THIOXO-1H-IMIDAZO[1,2-a]PURIN-9(4H)-ONE MONOHYDRATE

HRID 1154384
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Reaktionsgleichung

Reaktionsgleichung von HRID 1154384
[NH2:1][C:2]1[N:3]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:4]2[N:5]([CH2:11][CH2:12][N:13]=2)[C:6](=[O:10])[C:7]=1[N:8]=[O:9].[C:22](=S)=[S:23]>[Pd].CO>[OH2:9].[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:3]2[C:2]3[NH:1][C:22](=[S:23])[NH:8][C:7]=3[C:6](=[O:10])[N:5]3[CH2:11][CH2:12][N:13]=[C:4]23)=[CH:16][CH:17]=1
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Komponenten

5

Edukt 2

HCID 6348Carbon DisulfideHCID 178508072HCID 178508072, Verbindung

Produkt 1

HCID 202177034-[(4-CHLOROPHENYL)METHYL]-2,3,6,7-TETRAHYDRO-2-THIOXO-1H-IMIDAZO[1,2-a]PURIN-9(4H)-ONE MONOHYDRATE

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 5% palladium on carbon (1 g.) and 2.0 g. (0.0066 mole) of the product of Procedure 1 in MeOH (50 ml.) was hydrogenated until H2 uptake ceased. The catalyst was removed and carbon disulfide (0.5 g. 0.0066 mole) was added. The solution was refluxed for 4 hrs. and stirred at room temperature for 16 hrs. The mixture was concentrated in vacuo and the residue suspended in H2O (50 ml.), and refluxed for 6 hrs., cooled, and 1.55 g. of solid collected by filtration. The solid was dissolved in dil. NaOH, treated with activated carbon, and reprecipitated with HOAc to give 1.18 g. of product, m.p. 232°-235°.

Aufarbeitung

  1. customThe catalyst was removed
  2. temperatureThe solution was refluxed for 4 hrs
  3. concentrationThe mixture was concentrated in vacuo
  4. temperaturerefluxed for 6 hrs
  5. temperature, cooled
  6. filtrationof solid collected by filtration
  7. dissolutionThe solid was dissolved in dil. NaOH
  8. additiontreated with activated carbon
  9. customreprecipitated with HOAc
  10. customto give 1.18 g

Quellen und Nachweise

ORD-Eintrag
ord-d5d193d66b3443789de092eb2ec0a555
Quelldatensatz
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04489078

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