Octanoic Acid → HCID 23370109, compound

HRID 1901064Notes

Reaction equation

HRID 1901064 reaction equation
C[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:18])C=CC=CC=1.C([N:30]([CH2:33]C)CC)C.[NH2:35][C:36]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=1[NH:44][C:45](=[O:61])[C:46]1[CH:51]=[C:50]([C:52]([CH3:55])([CH3:54])[CH3:53])[C:49]([OH:56])=[C:48]([C:57]([CH3:60])([CH3:59])[CH3:58])[CH:47]=1>C1(C)C=CC=CC=1>[CH2:2]([NH:30][C:33](=[O:18])[NH:35][C:36]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=1[NH:44][C:45](=[O:61])[C:46]1[CH:51]=[C:50]([C:52]([CH3:53])([CH3:54])[CH3:55])[C:49]([OH:56])=[C:48]([C:57]([CH3:60])([CH3:59])[CH3:58])[CH:47]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 379Octanoic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 23370069HCID 23370069, compound

Product 1

HCID 23370109HCID 23370109, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

n-caprylic acid (0.32 g), diphenylphosphoryl azide (0.53 ml) and triethylamine (0.34 ml) were stirred in 10 toluene (5 ml) at room temperature for 3 hrs. and additionally for 2 hrs. at 80°-90° C. To the mixture was added under ice-cooling N-(2-amino-4-methoxyphenyl)-3,5-di-t-butyl-4-hydroxybenzamide (0.44 g), and the mixture was stirred overnight while returning slowly to room temperature. The solvent was distilled off and the residue was purified by a silica gel column chromatography (chloroform) to give N-[2-(3-heptylureido)-4-methoxyphenyl]-3,5-di-t-butyl-4-hydroxybenzamide (0.57 g, 93%) as a non-crystallizable solid.

Workup

  1. customat 80°-90° C
  2. additionTo the mixture was added under ice-
  3. customwhile returning slowly to room temperature
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by a silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-ca6a996ca918423a892cdd1b786b7ebd
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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