Dicyclohexylcarbodiimide → HCID 86750007, compound

HRID 1901062Notes

Reaction equation

HRID 1901062 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6](N)=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[C:13]([C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[C:20](O)=[O:21])([CH3:16])([CH3:15])[CH3:14].C1([N:37]=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([C:18]2[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])=[C:25]([OH:26])[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][C:19]=2[C:20]([NH2:37])=[O:21])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 86750007HCID 86750007, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-methoxy-2-nitroaniline (1.68 g), 3,5-di-t-butyl-4-hydroxybenzoic acid (2.50 g) and dicyclohexylcarbodiimide (2.06 g) were stirred in dichloromethane (12 ml) at room temperature for 6 days. After filtering off the insolubles and distilling off the solvent, the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=20:1) and crystallized from hexane-ethyl acetate to give N-(4-methoxy-2-nitrophenyl-3,5-di-t-butyl-4-hydroxybenzamide (1.56 g, 39%).

Workup

  1. filtrationAfter filtering off the insolubles
  2. distillationdistilling off the solvent
  3. customthe residue was purified by a silica gel column chromatography (hexane:ethyl acetate=20:1)
  4. customcrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-1ea00830510c494bbe34a472e1332642
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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