Methanol → 1-[2-(3-Carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[3-(1,5-dimethylpyrrol-2-yl)-phenoxy]-2-propanol

HRID 638065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638065
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH:16]2[O:18][CH2:17]2)[CH:9]=1.[NH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:31]=[C:27]([C:28]([NH2:30])=[O:29])[C:26]([OH:32])=[CH:25][CH:24]=1.CO>C(O)(C)C>[C:28]([C:27]1[CH:31]=[C:23]([CH:24]=[CH:25][C:26]=1[OH:32])[O:22][CH2:21][CH2:20][NH:19][CH2:17][CH:16]([OH:18])[CH2:15][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:3]2[N:2]([CH3:1])[C:6]([CH3:7])=[CH:5][CH:4]=2)[CH:9]=1)(=[O:29])[NH2:30]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 202551361,5-Dimethyl-2-[3-(2,3-epoxypropoxy)-phenyl]-pyrroleHCID 230496945-(2-Aminoethoxy)-2-hydroxybenzamide

Produkt 1

HCID 202551411-[2-(3-Carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[3-(1,5-dimethylpyrrol-2-yl)-phenoxy]-2-propanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

Solutions of 5.0 g of crude 1,5-dimethyl-2-[3-(2,3-epoxypropoxy)-phenyl]-pyrrole in 15 ml of isopropanol and of 3.0 g of 5-(2-aminoethoxy)-salicylamide in 30 ml of isopropanol are combined and boiled under reflux for 2.5 hours. A portion of the precipitated reaction product is dissolved by the addition of 50 ml of methanol. The filtered solution is evaporated to dryness and the residue is recrystallised twice from ethyl acetate, yielding 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[3-(1,5-dimethylpyrrol-2-yl)-phenoxy]-2-propanol having a melting point of 108°-112°.

Aufarbeitung

  1. temperatureunder reflux for 2.5 hours
  2. customA portion of the precipitated reaction product
  3. customThe filtered solution is evaporated to dryness
  4. customthe residue is recrystallised twice from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4c5e2b91807f4d00a1bedfc1d7f8310b
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04559354

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