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Methanol → HCID 178419254, Verbindung

HRID 1382534
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1382534
[CH2:1]([N:3]([CH2:38][CH3:39])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([NH:15][CH2:16][CH2:17][N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:28])=[C:10]3[S:29][C:30]4[CH:35]=[C:34]([O:36]C)[CH:33]=[CH:32][C:31]=4[C:8]([C:9]=23)=[N:7]1)[CH3:2].B(Br)(Br)[Br:41].CO>ClCCl>[BrH:41].[BrH:41].[CH2:38]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([NH:15][CH2:16][CH2:17][N:18]3[C:19](=[O:28])[C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:26]3=[O:27])=[C:10]3[S:29][C:30]4[CH:35]=[C:34]([OH:36])[CH:33]=[CH:32][C:31]=4[C:8]([C:9]=23)=[N:7]1)[CH3:39]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 144067742-[2-[[2-[2-(Diethylamino)ethyl]-8-methoxy-2H-[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]amino]ethyl]-1H-isoindole-1,3(2H)-dione

Produkt 1

HCID 178419254HCID 178419254, VerbindungAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

A 25° C. solution of 324.1 g (0.598 mol) of 2-[2-[[2-[2-(diethylamino)ethyl]-8-methoxy-2H-[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]amino]ethyl]-1H-isoindole-1,3(2H)-dione (2) in 7.45 L of dichloromethane was treated dropwise over 2 hr with 2.1 L (2.1 mol) of a 1M solution of boron tribromide in dichloromethane. The mixture was heated at reflux for 6.75 hr, treated with an additional 300 mL (0.3 mol) of boron tribromide solution, then further heated overnight. The refluxing mixture was treated cautiously with 1.86 L of methanol, heated an additional 12 hr, then cooled and stirred for 3 hr in an ice bath. The solids were collected by filtration, washed successively with dichloromethane and hexane, then dried at 220 mm/45° C./20 hr to give 291.8 g (70.8%) of 3, mp 232.5°- 234° C., 98.9% pure by HPLC.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6.75 hr
  3. temperaturefurther heated overnight
  4. temperatureheated an additional 12 hr
  5. temperaturecooled
  6. filtrationThe solids were collected by filtration
  7. washwashed successively with dichloromethane and hexane
  8. customdried at 220 mm/45° C./20 hr

Quellen und Nachweise

ORD-Eintrag
ord-720248306ade409c97e9af510acf7812
Quelldatensatz
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04806654

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