HCID 15083500, compound → HCID 22097678, compound

HRID 1458878Notes

Reaction equation

HRID 1458878 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][CH3:10])[C:3]=1[Cl:11].[Cl:12][C:13]1[CH:29]=[CH:28][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25](Cl)=[O:26])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1>C1(C)C(C)=CC=CC=1>[Cl:11][C:3]1[C:4]([CH2:8][O:9][CH3:10])=[N:5][CH:6]=[CH:7][C:2]=1[NH:1][C:25](=[O:26])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:16]2[CH:28]=[CH:29][C:13]([Cl:12])=[CH:14][CH:15]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 15083500HCID 15083500, compoundHCID 22097679HCID 22097679, compound

Product 1

HCID 22097678HCID 22097678, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

0.58 g (3.36 mmol) of 4-amino-3-chloro-2-methoxymethylpyridine was added to 0.94 g (3.36 mmol) of 4-(4-chloro-phenoxy)phenylacetyl chloride in 40 ml of xylene, and the mixture was refluxed for 8 hours. After the xylene had been removed in vacuo, the residue was taken up in methylene chloride. The mixture was washed with water and 0.1N aqueous sodium hydroxide solution, the combined aqueous phases were rendered neutral and extracted three times using ethyl acetate, and the ethyl acetate phase was dried over sodium sulfate. After the solvent had been removed in vacuo and the residue purified by column chromatography (silica gel, ethyl acetate:petroleum ether=80:20), 0.40 g of a yellow oil were obtained.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customAfter the xylene had been removed in vacuo
  3. washThe mixture was washed with water and 0.1N aqueous sodium hydroxide solution
  4. extractionextracted three times
  5. dry with materialthe ethyl acetate phase was dried over sodium sulfate
  6. customAfter the solvent had been removed in vacuo
  7. customthe residue purified by column chromatography (silica gel, ethyl acetate:petroleum ether=80:20)

Sources & evidence

ORD record
ord-29daa518a14a4e0e943bf81791cf2a76
Source dataset
uspto-grants-1998_12
Patent number
US05852042

Reaction notes

Loading…