Dicyclohexylcarbodiimide → HCID 23370082, compound

HRID 1901061Notes

Reaction equation

HRID 1901061 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[NH:10][C:11]([NH:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12].[C:19]([C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:31]=1[OH:32])[C:26]([OH:28])=O)([CH3:22])([CH3:21])[CH3:20].[CH:37]1(N=C=NC2CCCCC2)CCCC[CH2:38]1>ClCCl>[Cl:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]([NH:1][C:26](=[O:28])[C:25]2[CH:24]=[C:23]([C:19]([CH3:20])([CH3:21])[CH3:22])[C:31]([OH:32])=[C:30]([C:33]([CH3:34])([CH3:36])[CH3:35])[CH:29]=2)=[C:3]([NH:10][C:11]([NH:13][CH2:14][CH2:18][CH2:17][CH2:16][CH2:15][CH2:37][CH3:38])=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 23370094HCID 23370094, compound

Product 1

HCID 23370082HCID 23370082, compoundYield 161.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-amino-4,5-dichlorophenyl)-3-cyclopentylurea (0.48 g), 3,5-di-t-butyl-4-hydroxybenzoic acid (0.38 g) and dicyclohexylcarbodiimide (0.37 g) were stirred in dichloromethane (35 ml) at room temperature for 3 hrs. After filtering off the insolubles and distilling off the solvent, the residue was purified by a silica gel column chromatography (chloroform:ethyl acetate=20:1) to give N-[4,5-dichloro-2-(3-heptylureido)phenyl]-3,5-di-t-butyl-4-hydroxybenzamide (1.35 g, 68%) as crystals.

Workup

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

Sources & evidence

ORD record
ord-a07f5c7d937944acb8b5447fe15f2d15
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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