Chloroacetyl chloride → HCID 20554401, Verbindung

HRID 1106031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1106031
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]2[N:18]=[CH:19][N:20]=[CH:21][C:9]=2[C:8]1=[O:22]>O1CCOCC1.N1C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:7]([CH3:6])[C:8](=[O:22])[C:9]2[CH:21]=[N:20][CH:19]=[N:18][C:10]1=2)=[O:4]

Komponenten

5

Edukt 2

HCID 6577Chloroacetyl chlorideHCID 15535476HCID 15535476, Verbindung

Produkt 1

HCID 20554401HCID 20554401, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 312751,4-DioxaneLösungsmittel3×

Versuchsvorschrift

6.25 g (0.044 mol) of chloroacetyl chloride in 15 ml of absolute dioxan and 4.4 ml of dry pyridine in 15 ml of dioxan are added dropwise simultaneously (at 80° C. and in the course of 20 minutes) to a suspension of 4.6 g (0.020 mol) of 6-methyl-5,6-dihydropyrimido[4,5-b][1,5]benzodiazepin-5-one in 35 ml of absolute dioxan. The mixture is heated at the boil for a further 15 minutes and is then allowed to cool. The supernatant liquid is decanted off from the heavy dark phase, and the latter is washed with methylene chloride; the dioxan and methylene chloride phases are concentrated in vacuo. The oil which remains is dissolved in a little chloroform and filtered through neutral silica gel; the filtrate is evaporated and the residue is recrystallized from isopropanol, yield: 2.8 g, m.p. 176° to 178° C. (dec.).

Aufarbeitung

  1. temperatureThe mixture is heated at the boil for a further 15 minutes
  2. temperatureto cool
  3. customThe supernatant liquid is decanted off from the heavy dark phase
  4. washthe latter is washed with methylene chloride
  5. concentrationthe dioxan and methylene chloride phases are concentrated in vacuo
  6. dissolutionThe oil which remains is dissolved in a little chloroform
  7. filtrationfiltered through neutral silica gel
  8. customthe filtrate is evaporated
  9. customthe residue is recrystallized from isopropanol, yield: 2.8 g, m.p. 176° to 178° C. (dec.)

Quellen und Nachweise

ORD-Eintrag
ord-67b563c655d4460d91d14064a35be7de
Quelldatensatz
uspto-grants-1982_01
Patentnummer
US04311700

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