Sodium Hydroxide → 2-Thioxanthine

HRID 1108239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108239
ClC1C=C(C=CC=1)C[N:6]1[C:14]2[N:13]=[C:12](C(C)C)[NH:11][C:10]=2[C:9](=[O:18])[NH:8][C:7]1=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24].[OH-].[Na+]>N1C=CC=CC=1>[NH:8]1[C:9](=[O:18])[C:10]2[NH:11][CH:12]=[N:13][C:14]=2[NH:6][C:7]1=[S:24]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 184328393-(3-Chlorobenzyl)-8-isopropyl-xanthine

Produkt 1

HCID 12681852-ThioxanthineAusbeute 226,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

3.19 g of 3-(3-chlorobenzyl)-8-isopropyl-xanthine and 2.67 g of phosphorus pentasulfide were heated under reflux in 35 ml of pyridine for 5 hours. After cooling to -5° C., 13.2 ml (26.4 mM) of 2N NaOH were added over 15 minutes. The reaction mixture was evaporated to dryness, the residue suspended in water, the pH adjusted to 7.5 and the solid collected. The product was redissolved in 100 ml of 1N NaOH, treated with charcoal (5%), filtered and neutralized to pH 7.5. The solid was collected, washed and dried to give 2.29 g of crude thioxanthine. The product was dissolved in 250 ml of chloroform and filtered through 15 g of silica gel. The collected material was reprecipitated from NaOH by neutralization with HCl to give the title compound (2.38 g) as an off-white solid mp 218-20° C.

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. customthe solid collected
  3. dissolutionThe product was redissolved in 100 ml of 1N NaOH
  4. additiontreated with charcoal (5%)
  5. filtrationfiltered
  6. customThe solid was collected
  7. washwashed
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-957310a4632a4423971df6fe55709351
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066641

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