Propargyl bromide → 3'-Propargyloxy-2-methylbenzanilide

HRID 1578622Notes

Reaction equation

HRID 1578622 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 mixture 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.

Workup

  1. customwas prepared
  2. temperaturethe mixture 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-56f161f10d83481e9f3fa372fc854fe9
Source dataset
uspto-grants-1976_02
Patent number
US03937840

Reaction notes

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