N-(2-hydroxyethyl)-N'-(2-benzyloxybenzyl)urea → N-(2-hydroxyethyl)-N'-(2-hydroxybenzyl)urea

HRID 4537Notes

Reaction equation

HRID 4537 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15]CC1C=CC=CC=1)=[O:6]>CO.[Pd]>[OH:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])=[O:6]

Participants

4

Reactant 1

HCID 13754437N-(2-hydroxyethyl)-N'-(2-benzyloxybenzyl)urea

Product 1

HCID 13754438N-(2-hydroxyethyl)-N'-(2-hydroxybenzyl)urea

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

59.6 g of N-(2-hydroxyethyl)-N'-(2-benzyloxybenzyl)urea are dissolved in 600 ml of methanol and hydrogenated in the presence of 6 g of Pd/C-catalyst (5%). After 2 hours the hydrogenation ceases. The catalyst is suction-filtered, and the filtrate concentrated by evaporation in vacuo. The residue is recrystallised from 350 ml of ethyl acetate; the pure product melts at 100°-101°.

Workup

  1. filtrationThe catalyst is suction-filtered
  2. concentrationthe filtrate concentrated by evaporation in vacuo
  3. customThe residue is recrystallised from 350 ml of ethyl acetate

Sources & evidence

ORD record
ord-454c2953ea5c47808d6c09c24f3fa513
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Reaction notes

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