Lorazepam → HCID 10317256, Verbindung

HRID 2166686

Reaktionsgleichung

Reaktionsgleichung von HRID 2166686
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9]([OH:13])[N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:6]=2[CH:21]=1>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-].C(#N)C=C>[C:7]([CH2:6][CH2:5][N:11]1[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:21][C:6]=2[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[N:8][CH:9]([OH:13])[C:10]1=[O:12])#[N:8]

Komponenten

4

Edukt 1

HCID 3958Lorazepam

Produkt 1

HCID 10317256HCID 10317256, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 7855AcrylonitrileLösungsmittel

Versuchsvorschrift

1 g of Teba and 8 drops of a 40% methanolic solution of Triton B were added to a suspension of 10 g of 7-chloro-3-hydroxy-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one ("Lorazepam") in 50 ml of acrylonitrile and the mixture was stirred for 24 hours at room temperature. Then the reaction mixture was cooled to 4° C., the precipitate was filtered and recrystallized from ethyl acetate. 1-(2-Cyanoethyl)-7-chloro-3-hydroxy-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one, m.p. 198° to 202° C., was obtained. Without addition of Teba also the disubstituted 1-(2-cyanoethyl)-7-chloro-3-(2-cyanoethoxy)-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one, m.p. 210° to 213° C. (from acetonitrile), is obtained.

Aufarbeitung

  1. temperatureThen the reaction mixture was cooled to 4° C.
  2. filtrationthe precipitate was filtered
  3. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d4d29dc6bfde473fb2b3a8558eb506ee
Quelldatensatz
uspto-grants-1983_06
Patentnummer
US04388313

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