Diphenyl Ether → HCID 178486804, compound

HRID 1517880Notes

Reaction equation

HRID 1517880 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH:12]=[C:13]2[C:18](=[O:19])OC(C)(C)OC2=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O(C1C=CC=CC=1)C1C=CC=CC=1>CCCCCC>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[N:11]=[CH:12][CH:13]=[C:18]2[OH:19]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 212340935-[[(3,4-Dimethoxyphenyl)amino]methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 178486804HCID 178486804, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

5-((3,4-Dimethoxyphenylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (16.1 g, 52 mmol) was added to a pre-heated 1000 mL round-bottom flask containing 1-phenoxy benzene (100 mL) at 230° C. The reaction was stirred for 5 min, and then cooled to 120° C. n-Hexane (100 mL) was added to the solution to allow the product to precipitate out from the reaction solution. The mixture was further stirred at rt overnight. The solid was collected and crystallized in a solution of EtOAc/n-hexane (50 mL, v/v=10/1) to afford the title compound as a brown solid (10.2 g, 95%).

Workup

  1. additionwas added to the solution
  2. customto precipitate out from the reaction solution
  3. stirringThe mixture was further stirred at rt overnight
  4. customThe solid was collected
  5. customcrystallized in a solution of EtOAc/n-hexane (50 mL, v/v=10/1)

Sources & evidence

ORD record
ord-ba80023590bd4ddf88cd2f9fc023b57d
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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