Sodium Carbonate → 5-Chloro-1-(benzo[b]thien-3-ylmethyl)pyrimidin-2-one

HRID 434645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434645
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.ClC[C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[CH:15]=1.[C:20](=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:20][C:15]2[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[S:12][CH:11]=2)[CH:7]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 128138372-(Chloromethyl)-1-benzothiophene

Produkt 1

HCID 204917695-Chloro-1-(benzo[b]thien-3-ylmethyl)pyrimidin-2-oneAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred suspension of 5-chloropyrimidin-2-one (522 mg), 2-chloromethyl benzothiophene (910 mg), anhydrous sodium carbonate (850 mg) and benzyltrimethylammonium chloride (15 mg) in dry N,N-dimethylformamide (15 ml) was stirred at room temperature for 1 h and then at 80° C. for 45 min. The reaction mixture was then diluted with water (25 ml) and extracted with ethyl acetate (75 ml, 2×25 ml). The combined extracts were washed with water (2×50 ml), dried (MgSO4) and evaporated to a pale yellow solid which was crystallised twice from ethyl acetate to give white crystals of the title pyrimidinone (760 mg), m.p. 138°-140° C., λmax (EtOH) 227.5 nm (ε 32,540), 290.5 nm (ε 3,150), 298.5 nm (ε 3,760), 333.5 nm (ε 2,660).

Aufarbeitung

  1. waitat 80° C. for 45 min
  2. extractionextracted with ethyl acetate (75 ml, 2×25 ml)
  3. washThe combined extracts were washed with water (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a pale yellow solid which
  6. customwas crystallised twice from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-89210adc069349d6a472fe810292329a
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04399140

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