Sodium hydride → HCID 14303734, compound

HRID 2350968Notes

Reaction equation

HRID 2350968 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][C:14](=[O:17])[C:15]=2[CH3:16])=[CH:6][CH:5]=1.[CH2:30](I)[CH2:31][CH3:32]>CS(C)=O>[CH3:16][C:15]1[C:14](=[O:17])[CH:13]=[C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:30][CH2:31][CH3:32])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 14303742HCID 14303742, compound

Product 1

HCID 14303734HCID 14303734, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 50 ml of a suspension of 0.36 g (0.018 mole) of sodium hydride in DMSO, 1.7 g (0.0048 mole) of 2-(4-hydroxyphenyl)-3-methyl-1,6-diphenyl-4(1H)-pyridinone was added, followed by further dropwise addition of 1.0 g (0.0058 mole) of propyl iodide. The reaction mixture was then stirred at room temperature for 6 hours. The reaction mixture was thereafter poured into ice water, followed by extraction with chloroform. After washing the organic layer with water, it was dried over anhydrous magnesium sulfate. The solvent was distilled off, followed by recrystallization from a 2:1 mixed solvent of acetone and hexane to obtain 1.6 g of 3-methyl-1,6-diphenyl-2-(4-propoxyphenyl)-4(1H)-pyridinone having a melting point of 165°-168° C.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washAfter washing the organic layer with water, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customfollowed by recrystallization from a 2:1 mixed solvent of acetone and hexane

Sources & evidence

ORD record
ord-9b93c51cb9f449b3a409e282a4efaf62
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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