Dibenzylamine → N-[2-(3,3-dibenzylureido)phenyl]-3,5-di-t-butyl-4-hydroxybenzamide

HRID 1901050Notes

Reaction equation

HRID 1901050 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:27]=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:29]=1[OH:30])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18](=[O:26])OC1C=CC=CC=1)=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:35]([NH:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1C=CC=CC=1>[CH2:43]([N:42]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:18](=[O:26])[NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:8](=[O:9])[C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:29]([OH:30])=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:27]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 23370104HCID 23370104, compound

Product 1

HCID 23370061N-[2-(3,3-dibenzylureido)phenyl]-3,5-di-t-butyl-4-hydroxybenzamideYield 24%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phenyl N-[2-(3,5-di-t-butyl-4-hydroxybenzoylamino)phenyl]carbamate (1.6 g) and dibenzylamine (0.7 g) were dissolved in benzene (10 ml) and stirred at 70°-80°0 C. for 2 hrs. The reaction solution was washed with 2N sodium hydroxide, saturated ammonium chloride solution, dried over anhydrous NaSO4 and the solvent was distilled off. Purification of the residue by a silica gel column chromatography followed by crystallization from ether afforded N-[2-(3,3-dibenzylureido )phenyl]-3,5-di-t-butyl-4-hydroxybenzamide (0.47 g, 23%).

Workup

  1. washThe reaction solution was washed with 2N sodium hydroxide, saturated ammonium chloride solution
  2. dry with materialdried over anhydrous NaSO4
  3. distillationthe solvent was distilled off
  4. customPurification of the residue by a silica gel column chromatography
  5. customfollowed by crystallization from ether

Sources & evidence

ORD record
ord-d0532b8bf9924c39af8475eeb33a831e
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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