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Bromazepam → 7-bromo-2,3-dihydro-2-oxo-alpha-propyl-5-(2-pyridyl)-1H-1,4-benzodiazepine-1-acetic acid methyl ester

HRID 1580607
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1580607
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.C[O-].[Na+].CN(C)C=O.Br[CH:29]([CH2:34][CH2:35][CH3:36])[C:30]([O:32][CH3:33])=[O:31]>O.C1(C)C=CC=CC=1>[CH3:33][O:32][C:30](=[O:31])[CH:29]([CH2:34][CH2:35][CH3:36])[N:11]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:19][C:6]=2[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:8][CH2:9][C:10]1=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 2441BromazepamHCID 6228DimethylformamideHCID 529992Methyl 2-bromopentanoateHCID 10942334Sodium Methoxide

Produkt 1

HCID 543891827-bromo-2,3-dihydro-2-oxo-alpha-propyl-5-(2-pyridyl)-1H-1,4-benzodiazepine-1-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 0.1 mole of 7-bromo-1,3-dihydro-5-(2-pyridyl)-2H-1,4-benzodiazepin-2-one and 0.11 mole of sodium methoxide in about 200 ml. of dimethylformamide is heated at about 95° c. for about 20 minutes. To the mixture is added a solution of 0.11 mole of methyl 2-bromovalerate in about 200 ml. of toluene over a period of about 1 hour at about 95° C., and heating is continued for an additional period of about 6 hours. The reaction mixture is then evaporated in vacuo and the residue thus obtained is stirred with about 500 ml. of water. The resulting suspension is filtered and the solids thus obtained are crystallized from a suitable organic solvent such as ether, methanol, methylene chloride, methylene chloride-methanol and the like to obtain 7-bromo-2,3-dihydro-2-oxo-α-propyl-5-(2-pyridyl)-1H-1,4-benzodiazepine-1-acetic acid methyl ester.

Aufarbeitung

  1. temperatureheating
  2. waitis continued for an additional period of about 6 hours
  3. customThe reaction mixture is then evaporated in vacuo
  4. customthe residue thus obtained
  5. filtrationThe resulting suspension is filtered
  6. customthe solids thus obtained
  7. customare crystallized from a suitable organic solvent such as ether, methanol, methylene chloride, methylene chloride-methanol

Quellen und Nachweise

ORD-Eintrag
ord-c162350d230341889fa0982c0460e1bc
Quelldatensatz
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03933816

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