Dicyclohexylcarbodiimide → HCID 23370117, compound

HRID 1901057Notes

Reaction equation

HRID 1901057 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].[C:18]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:30]=1[OH:31])[C:25]([OH:27])=O)([CH3:21])([CH3:20])[CH3:19].[CH:36]1(N=C=NC2CCCCC2)CCCC[CH2:37]1>ClCCl>[F:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][C:10]([NH:12][CH2:13][CH2:17][CH2:16][CH2:15][CH2:14][CH2:36][CH3:37])=[O:11])=[C:2]([NH:1][C:25](=[O:27])[C:24]2[CH:23]=[C:22]([C:18]([CH3:19])([CH3:20])[CH3:21])[C:30]([OH:31])=[C:29]([C:32]([CH3:33])([CH3:35])[CH3:34])[CH:28]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 23370136HCID 23370136, compound

Product 1

HCID 23370117HCID 23370117, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-amino-4-fluorophenyl)-3-cyclopentylurea (1.07 g), 3,5-di-t-butyl-4-hydroxybenzoic acid (1.00 g) and dicyclohexylcarbodiimide (0.99 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=10:1) to yield N-[5-fluoro-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=10:1)

Sources & evidence

ORD record
ord-631c8d15f8bd444a9d4c53daa1341b2b
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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