5-[2-(Benzylamino)-ethoxy]-salicylamide → 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol

HRID 638060Notes

Reaction equation

HRID 638060 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:6]=1.[CH2:17]([NH:24][CH2:25][CH2:26][O:27][C:28]1[CH:36]=[C:32]([C:33]([NH2:35])=[O:34])[C:31]([OH:37])=[CH:30][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(C)C>[CH2:17]([N:24]([CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([OH:37])=[C:32]([C:33](=[O:34])[NH2:35])[CH:36]=1)[CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 137544195-[2-(Benzylamino)-ethoxy]-salicylamideHCID 202551882-[4-(2,3-Epoxypropoxy)-phenyl]-thiazole

Product 1

HCID 202550681-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 6.50 g of 2-[4-(2,3-epoxypropoxy)-phenyl]-thiazole and 7.25 g of 5-[2-(benzylamino)-ethoxy]-salicylamide in 150 ml of isopropanol is heated under reflux for 18 hours and the solvent is subsequently removed in a rotary evaporator. The 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol, obtained in the form of an oil, is further processed in that form.

Workup

  1. temperatureunder reflux for 18 hours
  2. customthe solvent is subsequently removed in a rotary evaporator

Sources & evidence

ORD record
ord-4ea1db641b884f5e8568bec31e2b75aa
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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