4-Aminophenol → HCID 11036589, compound

HRID 973900Notes

Reaction equation

HRID 973900 reaction equation
[C:1]([OH:22])(=O)[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C1N=CN(C(N2C=NC=C2)=O)C=1.[OH:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1>O>[OH:35][C:36]1[CH:42]=[CH:41][C:39]([NH:40][C:1](=[O:22])[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 17815,8,11-Eicosatriynoic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 11036589HCID 11036589, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In the same manner as in the above example, the intermediate formed from 1 g of 5,8,11-eicosatriynoic acid and 0.7 g of CDI is treated with 0.727 g of para-hydroxyaniline. The medium is then stirred for 24 hours at room temperature. Water is then added gradually to the mixture until all the product formed precipitates. It is drained and dried and then recrystallized in isopropyl ether. 0.85 g of N-(para-hydroxyphenyl)-5,8,11-eicosatriynamide is obtained in the form of beige-white crystals of melting point 121° C.

Workup

  1. customformed
  2. customprecipitates
  3. customdried
  4. customrecrystallized in isopropyl ether

Sources & evidence

ORD record
ord-ae4f3a07d81645559d9ed85252a992c6
Source dataset
uspto-grants-1991_11
Patent number
US05066427

Reaction notes

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