O-Phenylenediamine → N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamide

HRID 1901048Notes

Reaction equation

HRID 1901048 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C.[C:41]1([NH2:48])[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[NH2:47]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH2:47][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[NH:48][C:8](=[O:10])[C:7]1[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:13]([OH:14])=[C:12]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:11]=1

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acid

Product 1

HCID 23370116N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamideYield 32.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-di-t-butyl-4-hydroxybenzoic acid (5.0 g) in methylene chloride (20 ml) was added dicyclohexylcarbodiimide (2.17 g) and the mixture was stirred overnight at room temperature. Subsequently, triethylamine (2.1 ml), 4-dimethylaminopyridine (0.37 g) and o-phenylenediamine (1.08 g) were added and the mixture was stirred overnight at room temperature. The insolubles was filtered off and the filtrate was concentrated to dryness. The residue was purified by a silica gel column chromatography (chloroform:ethyl acetate=20:1) and crystallized from diisopropyl ether to give N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamide (1.10 g, 32%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationThe insolubles was filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was purified by a silica gel column chromatography (chloroform:ethyl acetate=20:1)
  5. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-971f76d4d15449d0ab5c868d448dc7b5
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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