Thiourea → HCID 178508225, Verbindung

HRID 848086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 848086
[NH2:1][C:2](N)=[S:3].[NH2:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH2:15][O:16][CH2:17][CH2:18][O:19]C(=O)C2C=CC=CC=2)=C(Cl)N=1>C(O)(C)C>[OH:19][CH2:18][CH2:17][O:16][CH2:15][N:12]1[CH:11]=[N:10][C:9]2[C:2](=[S:3])[NH:1][C:6]([NH2:5])=[N:14][C:13]1=2

Komponenten

4

Edukt 2

HCID 2723790ThioureaHCID 137857472-Amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine

Produkt 1

HCID 178508225HCID 178508225, VerbindungAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Thiourea (0.28 g) was added to a refluxing solution of 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (1.27 g) in isopropanol (40 ml). The reaction mixture was heated at reflux for 11/2 hours and then chilled. 9-(2-benzoyloxyethoxymethyl)-thioguanine (0.58 g, m.p. 199°-202° C.) was removed by filtration. This was added to 40 ml of aqueous ammonia (about 7 N) and the mixture heated on a steam bath for 10 minutes and then stirred overnight at room temperature. The water and ammonia were removed in vacuo and the residue triturated with acetone and then with ether to remove benzamide. The remaining solid was recrystallized twice from water to give yellow flakes of 9-(2-hydroxyethoxymethyl)thioguanine (0.26 g, m.p. 251°-254° C.).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 11/2 hours
  3. temperaturechilled
  4. custom9-(2-benzoyloxyethoxymethyl)-thioguanine (0.58 g, m.p. 199°-202° C.) was removed by filtration
  5. additionThis was added to 40 ml of aqueous ammonia (about 7 N)
  6. temperaturethe mixture heated on a steam bath for 10 minutes
  7. customThe water and ammonia were removed in vacuo
  8. customthe residue triturated with acetone
  9. customwith ether to remove benzamide
  10. customThe remaining solid was recrystallized twice from water

Quellen und Nachweise

ORD-Eintrag
ord-0282396aac7e4c6098c5d9a1f7e4280f
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04294831

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