Pyridine → HCID 178522340, Verbindung

HRID 1735952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1735952
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(N[N:16]1[CH:24]=[C:22](C)[C:20](=O)[NH:19][C:17]1=[O:18])=O.[N:25]1C=CC=CC=1>>[CH2:1]([O:8][C:9]([NH:25][C:20]1[CH:22]=[CH:24][NH:16][C:17](=[O:18])[N:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 19076265HCID 19076265, Verbindung

Produkt 1

HCID 178522340HCID 178522340, Verbindung

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Over a period of about 1 h, benzyloxycarbonyl chloride (52 ml; 0.36 mol) was added dropwise to a suspension of cytosine (8, 20.0 g; 0.18 mol) in dry pyridine (1000 ml) at 0° C. under nitrogen in oven-dried equipment. The solution then was stirred overnight, after which the pyridine suspension was evaporated to dryness, in vacuo. Water (200 ml) and 4N hydrochloric acid were added to reach pH~1. The resulting white precipitate was filtered off, washed with water and partially dried by air suction. The still-wet precipitate was boiled with absolute ethanol (500 ml) for 10 min, cooled to 0° C., filtered, washed thoroughly with ether, and dried, in vacuo. Yield 24.7 g (54%). M.p.>250° C. Anal. for C12H11N3O3. Found (calc.); C: 58.59(58.77); H: 4.55(4.52); N: 17.17(17.13). No NMR spectra were recorded since it was not possible to get the product dissolved.

Aufarbeitung

  1. customafter which the pyridine suspension was evaporated to dryness, in vacuo
  2. additionWater (200 ml) and 4N hydrochloric acid were added
  3. filtrationThe resulting white precipitate was filtered off
  4. washwashed with water
  5. custompartially dried by air suction
  6. waitThe still-wet precipitate was boiled with absolute ethanol (500 ml) for 10 min
  7. filtrationfiltered
  8. washwashed thoroughly with ether
  9. customdried, in vacuo
  10. customto get the product
  11. dissolutiondissolved

Quellen und Nachweise

ORD-Eintrag
ord-09ecc43c3f1649fb90123f272f8df593
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05539082

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