1,4-Bis[4-[(1-benzyloxyureido)methyl]phenoxy]butane → 1,4-Bis[4-[(1-hydroxyureido)methyl]phenoxy]butane

HRID 263537

Reaction equation

HRID 263537 reaction equation
C([O:8][N:9]([CH2:13][C:14]1[CH:44]=[CH:43][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]([O:35]CC3C=CC=CC=3)[C:32]([NH2:34])=[O:33])=[CH:26][CH:25]=2)=[CH:16][CH:15]=1)[C:10]([NH2:12])=[O:11])C1C=CC=CC=1.[H][H]>CN(C)C=O.C(O)C.[C].[Pd]>[OH:35][N:31]([CH2:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:17]2[CH:43]=[CH:44][C:14]([CH2:13][N:9]([OH:8])[C:10]([NH2:12])=[O:11])=[CH:15][CH:16]=2)=[CH:25][CH:26]=1)[C:32]([NH2:34])=[O:33]

Participants

5

Reactant 2

HCID 542130111,4-Bis[4-[(1-benzyloxyureido)methyl]phenoxy]butaneHCID 178418361HCID 178418361, compound

Product 1

HCID 542604191,4-Bis[4-[(1-hydroxyureido)methyl]phenoxy]butaneYield 62%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

1,4-Bis[4-[(1-benzyloxyureido)methyl]phenoxy]butane (1.94 g) was dissolved in 45 ml of dimethylformamide-ethanol (8:1), mixed with 0.29 g of 10% palladium carbon and then the mixture was stirred for 22 hours at room temperature in an atmosphere of hydrogen. The catalyst was removed by filtration using Celite, and the solvent was evaporated under a reduced pressure to obtain 0.84 g of 1,4-bis[4-[(1-hydroxyureido)methyl]phenoxy]butane.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-0864f6c93e4148b1b8946b1cc0b66e5f
Source dataset
uspto-grants-1997_07
Patent number
US05643931

Linked notes

Loading…