Propargyl bromide → 3'-Propargyloxy-2-methylbenzanilide

HRID 1287695Notes

Reaction equation

HRID 1287695 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].[CH2:18](Br)[C:19]#[CH:20].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[C:19]#[CH:18]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 11401898Benzamide, N-(3-hydroxyphenyl)-2-methyl-

Product 1

HCID 215064553'-Propargyloxy-2-methylbenzanilideYield 87.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 22.7 g (0.1 mol) of 3'-hydroxy-2-methylbenzanilide, 11.9 g (0.1 mol) of propargylbromide, 10.6 g (0.1 mol) of sodium carbonate and 250 ml of acetone was prepared and the nixture was refluxed for 4 hours with stirring. After cooling, the reaction mixture was filtered and the acetone was removed by distillation. The residual material was dissolved in benzene, washed with water and dehydrated over anhydrous sodium sulfate. The benzene was removed and the product was recrystallized from aqueous ethanol to obtain a 23.2 g (87.7%) of fine white needles having a melting point of 93°-95° C. EXAMPLE 8

Workup

  1. customwas prepared
  2. temperaturethe nixture was refluxed for 4 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customthe acetone was removed by distillation
  6. dissolutionThe residual material was dissolved in benzene
  7. washwashed with water
  8. customThe benzene was removed
  9. customthe product was recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-e4154cfbfd654bf4a136d31610a08a46
Source dataset
uspto-grants-1976_10
Patent number
US03985804

Reaction notes

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