Diphenyl Ether → HCID 178469503, compound

HRID 925500Notes

Reaction equation

HRID 925500 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]([C:14]([O-:16])=O)[C:11]([O-:13])=[O:12])=[CH:4][CH:3]=1.[C:17]1(OC2C=CC=CC=2)C=CC=C[CH:18]=1>C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:17][CH3:18])=[O:12])=[C:14]2[OH:16]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 86714216HCID 86714216, compound

Product 1

HCID 178469503HCID 178469503, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Diethyl(2-(((6-bromopyridin-3-yl)amino)methylene)malonate (40 g, 0.117 mol) was added to boiling diphenyl ether (214 mL) in batches over 5 min, heated under reflux for 45 min. After confirming a disappearance of the raw materials by a thin layer chromatography plate (ethyl acetate:petroleum ether=1:3), the reaction mixture was cooled and poured into petroleum ether to precipitate a solid, suction filtered to give 24.6 g of a khaki solid.

Workup

  1. customover 5 min
  2. temperatureheated
  3. temperatureunder reflux for 45 min
  4. temperaturethe reaction mixture was cooled
  5. customto precipitate a solid, suction
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c98cf408f0da44a88b69d31b9244e7f5
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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