Hydrochloric Acid → 2-Chloromethyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one

HRID 910197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910197
Cl.C(O[C:5]([C:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][S:9][C:8]=1[NH2:18])=[O:6])C.[Cl:19][CH2:20][C:21]#[N:22].C(=O)([O-])O.[Na+]>O1CCOCC1.O>[Cl:19][CH2:20][C:21]1[NH:22][C:5](=[O:6])[C:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][S:9][C:8]=2[N:18]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 23741772-Chloromethyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-oneAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Hydrogen chloride gas was bubbled through a stirred solution of 2-amino-4-phenylthiophene-3-carboxylic acid ethyl ester (4.94 g, 0.02 mol) and chloroacetonitrile (1.4 ml, 0.022 mol) in anhydrous 1,4-dioxane (60 ml) for about 4 hours. A thick suspension formed initially which slowly dissolved. The mixture was stirred at ambient temperature for 18 hours before being poured into water (250 ml) and basified (pH 8) by the addition of sodium hydrogen carbonate. The supernatant was then decanted to leave a gummy solid which was triturated with aqueous ethanol to give 2-chloromethyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one as a yellow solid (3.70 g), which was used without further purification.

Aufarbeitung

  1. customA thick suspension formed initially which
  2. dissolutionslowly dissolved
  3. customThe supernatant was then decanted
  4. customto leave a gummy solid which
  5. customwas triturated with aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-11a41cd258654b6fa56b95d665d6651d
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022076B2

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