Propranolol Hydrochloride → HCID 53833412, Verbindung

HRID 845723

Reaktionsgleichung

Reaktionsgleichung von HRID 845723
[CH3:1][CH:2]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:3].Cl.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.Cl[C:38]([O:40][CH:41]([Cl:43])[CH3:42])=[O:39]>C(Cl)(Cl)Cl>[Cl:43][CH:41]([O:40][C:38]([N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:39])[CH3:42]

Komponenten

5

Edukt 3

HCID 62882Propranolol HydrochlorideHCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformate

Produkt 1

HCID 53833412HCID 53833412, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A suspension of propanolol hydrochloride (3.0 g) in chloroform (100 ml) was mixed with proton sponge® (4.3 g) and cooled in an ice bath. 1-Chloroethyl chloroformate (1.5 g) was added dropwise to the reaction mixture. The suspension dissolved in about 5 minutes. The cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours. The chloroform solution was washed with water, 3N HCl and water successively. The organic layer was dried over Na2SO4 and evaporated to a thick oil weighing 3.6 g. NMR (CDCl3) δ1.25 (6H, d, J=7 Hz, CH(Me)2), 1.8 (3H, d, J=7 Hz, CH3CH), 3.3=3.6 (3H, m, ArOCH2 and CH(Me)2), 4.0-4.6 (3H, m, NCH2 and CHOH), 6.61 (1H, q, J=7 Hz, CH3CH) and 6.7-8.4 (7H, m, aromatic). IR (film) ν3450, 1715, 1583, 1270, 1248, 1108 cm-1.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. dissolutionThe suspension dissolved in about 5 minutes
  3. customThe cooling bath was removed
  4. washThe chloroform solution was washed with water, 3N HCl and water successively
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated to a thick oil

Quellen und Nachweise

ORD-Eintrag
ord-7dc69a75ea4c464c9a630191f4f46948
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04760057

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