Methyl 2-bromo-3-nitrobenzoate → 9-Nitro-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one

HRID 1491620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1491620
Br[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.O.[CH2:16]([NH2:19])[CH2:17][NH2:18]>C(O)CCC>[N+:12]([C:11]1[C:2]2[NH:19][CH2:16][CH2:17][NH:18][C:4](=[O:6])[C:3]=2[CH:8]=[CH:9][CH:10]=1)([O-:14])=[O:13]

Komponenten

4

Edukt 2

HCID 79263Methyl 2-bromo-3-nitrobenzoateHCID 12200817Ethylenediamine monohydrate

Produkt 1

HCID 27716119-Nitro-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 11.7 parts of methyl 2-bromo-3-nitrobenzoate, 8.1 parts of 1,2-ethanediamine monohydrate and 40 parts of 1-butanol was stirred for 1/2 at reflux temperature. The reaction mixture was evaporated and the residue was diluted with 50 parts of water. The precipitate was filtered off and washed with water and 2-propanol. It was then recrystallized from 2-methoxyethanol, yielding 6.5 parts of 2,3,4,5-tetrahydro-9-nitro-1H-1,4-benzodiazepin-5-one; mp. 191°-195° C. (interm. 1).

Aufarbeitung

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionthe residue was diluted with 50 parts of water
  4. filtrationThe precipitate was filtered off
  5. washwashed with water and 2-propanol
  6. customIt was then recrystallized from 2-methoxyethanol

Quellen und Nachweise

ORD-Eintrag
ord-b5bb6de2332b49a1ae470df8ba774161
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371079

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