3,5-Di-tert-butyl-4-hydroxybenzoic acid → HCID 23370125, compound

HRID 1901068Notes

Reaction equation

HRID 1901068 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[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](O)=[O:27])([CH3:22])([CH3:21])[CH3:20].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:12]([NH:11][C:9](=[O:10])[NH:8][C:3]1[C:2]([NH:1][C:26](=[O:27])[C:25]2[CH:29]=[C:30]([C:33]([CH3:34])([CH3:35])[CH3:36])[C:31]([OH:32])=[C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:24]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23370063HCID 23370063, compound

Product 1

HCID 23370125HCID 23370125, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3-amino-2-pyridyl)-3-heptylurea (0.80 g), 3,5-di-t-butyl-4-hydroxybenzoic acid (0.80 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride (0.67 g) was 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:methanol=30:1) to give N-[2-(3-heptylureido)-3-pyridyl]-3,5-di-t-butyl-4-hydroxybenzamide (1.34 g, 87%) as a non-crystallizable solid.

Workup

  1. filtrationAfter filtering off the insolubles
  2. distillationdistilling off the solvent
  3. customthe residue was purified by a silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-b3750a3ee8214970860c7a5d3d0b6799
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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