Methyl chloroformate → Methyl 1,2,4,5-tetrahydro-3h-3-benzazepine-3-carboxylate

HRID 327399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327399
[OH-].[Na+].[CH2:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][NH:5][CH2:4]1.Cl[C:15]([O:17][CH3:18])=[O:16]>O>[CH3:18][O:17][C:15]([N:5]1[CH2:4][CH2:3][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6]1)=[O:16]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine

Produkt 1

HCID 22219599Methyl 1,2,4,5-tetrahydro-3h-3-benzazepine-3-carboxylateAusbeute 958,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In 150 ml of water was dissolved 4.13 g (0.10 mol). of sodium hydroxide. To the solution was added 15.27 g (10.4 mmol.) of 2,3,4,5-tetrahydro-1H-3-benzazepine. The reaction mixture was cooled with ice, and there was added dropwise 7.9 ml (0.10 mol.) of methyl chloroformate. The mixture was stirred for 2.5 hours at room temperature, then extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off to leave 20.46 g (96%) of 3-methoxycarbonyl-2,3,4,5-tetrahydro-1H-3-benzazepine as colorless crystals. Recrystallization from diethyl ether--n-hexane gave colorless needles, m.p. 53°-54° C. Elemental Analysis for C12H15NO2 :

Aufarbeitung

  1. temperatureThe reaction mixture was cooled with ice, and there
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-8bfa6c66847e4a33a09e03227af4c389
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273974

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