Chlorosuccinimide → 5-chloro-6-ethyl-2-phenyl-4(3H)-pyrimidinone

HRID 1449

Reaktionsgleichung

Reaktionsgleichung von HRID 1449
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:5](=[O:15])[CH:4]=1)[CH3:2].[Cl:16]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:16][C:4]1[C:5](=[O:15])[NH:6][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:8][C:3]=1[CH2:1][CH3:2]

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 1356298226-Ethyl-2-phenylpyrimidin-4(1H)-one

Produkt 1

HCID 1358375365-chloro-6-ethyl-2-phenyl-4(3H)-pyrimidinoneAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A stirred solution of 7.81 g (39.1 mmol) of 6-ethyl-2-phenyl-4(3H)-pyrimidinone and 5.80 g (43.4 mmol) of N-chlorosuccinimide in 100 mL of glacial acetic acid was heated at 90° C. for 4 h. The mixture was cooled, poured onto crushed ice and allowed to stand until the ice had melted. The mixture was filtered and the solid collected was washed with water and a little ether. The solid was dried in a vacuum oven at 50C to afford 7.99 g of 5-chloro-6-ethyl-2-phenyl-4(3H)-pyrimidinone (an intermediate for compound 172) as a white solid. 1H-NMR (d6-DMSO) 1.30(3H,t), 2.8(2H,q), 7.6(3H,m), 8.2(2H.m).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationThe mixture was filtered
  5. customthe solid collected
  6. washwas washed with water
  7. dry with materialThe solid was dried in a vacuum oven at 50C

Quellen und Nachweise

ORD-Eintrag
ord-475d4575be964743a02cc9754560986f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726124

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