Hydrochloric Acid → N-methyl-2-(2-methylphenyl)-2-oxoacetamide

HRID 256765Notes

Reaction equation

HRID 256765 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:11][N+:12]#[C-:13].C(=O)([O-])[O-:15].[Ca+2].Cl>CC(C)=O.O>[CH3:13][NH:12][C:11](=[O:15])[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 11646Methyl isocyanideHCID 702762-Methylbenzoyl chloride

Product 1

HCID 15239356N-methyl-2-(2-methylphenyl)-2-oxoacetamideYield 96.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-methylbenzoyl chloride (1.55 g) and methyl isocyanide (492 mg) was stirred at 60° C. for 6 hours. Then, the mixture was diluted with acetone (20 ml), and water (4 ml) and calcium carbonate (1.00 g) were added. The stirring of the resulting mixture was continued for 1 hour. The mixture was neutralized with dilute hydrochloric acid and extracted with methylene chloride. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with hexane-ethyl acetate (5:1) to obtain the title compound (1.71 g, Yield: 96.6%).

Workup

  1. additionwere added
  2. stirringThe stirring of the resulting mixture
  3. waitwas continued for 1 hour
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. washeluted with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-4cbdbcbd090d4529aad1d720771b1dfc
Source dataset
uspto-grants-1993_11
Patent number
US05258551

Reaction notes

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