4-Chlorophenol → HCID 54245348, compound

HRID 1031504Notes

Reaction equation

HRID 1031504 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=2)=[CH:21][C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:23])=[CH:16][N:15]=1>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=3)=[CH:21][C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:23])=[CH:16][N:15]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 53647660HCID 53647660, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54245348HCID 54245348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (20 ml) was dissolved 4-chlorophenol (330 mg). To the solution was added, while stirring, 60% sodium hydride (dispersion in paraffin) (103 mg). When exothermic reaction and evolution of hydrogen gas ceased, 4-[3-(2-chloro-5-pyridyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine (500 mg) and cuprous iodide (24 mg) were added to the reaction mixture, followed by stirring for 5 hours at 150° C. The reaction mixture was poured into water, which was subjected to extraction with dichloromethane. The extract solution was dried over anhydrous magnesium sulfate, which was then concentrated. The concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate) to obtain 4-[3-(2-(4-chlorophenoxy)-5-pyridyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine (Compound No. 3 ) (420 mg) as a resinous solid.

Workup

  1. additionTo the solution was added
  2. stirringby stirring for 5 hours at 150° C
  3. extractionwas subjected to extraction with dichloromethane
  4. dry with materialThe extract solution was dried over anhydrous magnesium sulfate, which
  5. concentrationwas then concentrated
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate)

Sources & evidence

ORD record
ord-a241ff3f6c3f4ff3a8c42a660865f2ee
Source dataset
uspto-grants-1990_09
Patent number
US04954497

Reaction notes

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