(4-Aminophenoxy)benzene → HCID 21082455, compound

HRID 347290Notes

Reaction equation

HRID 347290 reaction equation
C(O[C:4](=[O:27])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:10][CH:9]=1)=[O:6])C.[O:28]([C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(C)([O-])C.[Li+]>C1(C)C(C)=CC=CC=1>[CH2:15]([O:14][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[C:4]([NH:39][C:38]2[CH:37]=[CH:36][C:35]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:41][CH:40]=2)=[O:27])=[CH:13][CH:12]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 58800192HCID 58800192, compound

Product 1

HCID 21082455HCID 21082455, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of N-(4-dodecyloxyphenyl)oxalamic acid ethyl ester (10 g, 0.026 mol), 4-phenoxyaniline (5 g, 0.026 mol) and lithium t-butoxide (0.2 g, 0.0026 mol) in xylene (50 mL) isheated to gentle reflux. A distillate of ethanol/xylene is slowly collected; the reaction volumn is kept at 50 mL by adding xylene. Heating and distillation continued for 3 hours. The reaction mixture is cooled, the solids are collected and washed sequentially with warm ethyl acetate, ethanol, water and finally ethanol. There is obtained 11.5 g white solid mp: 179–181.

Workup

  1. distillationA distillate of ethanol/xylene is slowly collected
  2. additionby adding xylene
  3. temperatureHeating
  4. distillationdistillation
  5. temperatureThe reaction mixture is cooled
  6. customthe solids are collected
  7. washwashed sequentially with warm ethyl acetate, ethanol, water and finally ethanol

Sources & evidence

ORD record
ord-c83d14d0d1a1466eb5aa57dc263e76ab
Source dataset
uspto-grants-2007_02
Patent number
US07173128B2

Reaction notes

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