Propargyl bromide → HCID 14303621, compound

HRID 845315Notes

Reaction equation

HRID 845315 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([N:10]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13](=[O:22])[C:12]([CH3:23])=[C:11]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:8][CH:9]=1.[CH2:30](Br)[C:31]#[CH:32]>CS(C)=O>[CH3:23][C:12]1[C:13](=[O:22])[CH:14]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:32][C:31]#[CH:30])[CH:5]=2)[C:11]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 14303577HCID 14303577, compound

Product 1

HCID 14303621HCID 14303621, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 50 ml of a suspension of 0.72 g (0.03 mole) of sodium hydride in DMSO, 3.5 g (0.01 mole) of 1-(3-hydroxyphenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone was added, followed by further dropwise addition of 1.4 g (0.012 mole) of propargyl bromide. The reaction mixture was thereafter poured into ice water, followed by extraction with chloroform. After washing the organic layer (the extract) 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 1.5 g of 3-methyl-2,6-diphenyl-1-(3-propargyloxyphenyl)-4(1H)-pyridinone having a melting point of 166°-169° C.

Workup

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

Sources & evidence

ORD record
ord-39c8307a423b4d0d8841156e1bc184e1
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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