Diphenyl Ether → HCID 178469639, compound

HRID 2378095Notes

Reaction equation

HRID 2378095 reaction equation
C(O[C:4](=[O:18])[C:5](=[CH:11][NH:12][C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C>[CH2:9]([O:8][C:6]([C:5]1[C:4]([OH:18])=[C:14]2[S:15][CH:16]=[CH:17][C:13]2=[N:12][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 2807580Diethyl 2-((thiophen-3-ylamino)methylene)malonate

Product 1

HCID 178469639HCID 178469639, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add 2-(thiophen-3-ylaminomethylene)-malonic acid diethyl ester (7.66 g, 28.4 mmol) to refluxing phenyl ether (100 ml) over a period of 5 min under nitrogen. After the addition is complete, keep the reaction under reflux for 30 min. Cool the reaction mixture to room temperature, and then pour it into ethyl acetate (1000 ml). Collect the brown precipitate by filtration to obtain 7-hydroxy-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (4.82 g, 76%). MS (ES+): 224 (M+H); (ES−): 222 (M−H).

Workup

  1. additionAfter the addition
  2. customthe reaction
  3. temperatureunder reflux for 30 min
  4. customCollect the brown precipitate
  5. filtrationby filtration

Sources & evidence

ORD record
ord-945879bcde8e4db5b02958cab51e039d
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

Loading…