Methyl iodide → 5-Chloro-N,N,2-trimethyl-3-phenyl-2H-isoindole-1-carboxamide

HRID 1973315Notes

Reaction equation

HRID 1973315 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6]([CH3:21])[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]2[C:13]=1[CH:12]=[CH:11][C:10]([Cl:14])=[CH:9]2)=[O:4].[CH3:22]I>CN(C)C=O>[CH3:1][N:2]([CH3:22])[C:3]([C:5]1[N:6]([CH3:21])[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]2[C:13]=1[CH:12]=[CH:11][C:10]([Cl:14])=[CH:9]2)=[O:4]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 54545674HCID 54545674, compound

Product 1

HCID 537655045-Chloro-N,N,2-trimethyl-3-phenyl-2H-isoindole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 9.0 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid methylamide in 120 ml. of dimethylformamide is treated under argon at 0° C. with 5.0 g. of potassium tert. butylate and then stirred in an ice-bath for 30 minutes. At 0°-5° C. there are added 8 ml. of methyl iodide in one batch, the mixture is subsequently stirred for 2 hours at room temperature and poured onto 2 liters of ice-water. After the addition of 100 g. of sodium chloride, the separated oil is extracted with methylene chloride. The organic phase is washed with a solution of sodium chloride, dried over sodium sulfate and concentrated to dryness under reduced pressure. The oily residue is dissolved in 200 ml. of hot hexane. The solution obtained is cooled in an ice-bath, colorless crystals separating, and there is obtained 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid dimethylamide having a melting point of 86°-88° C.

Workup

  1. additionA suspension of 9.0 g
  2. additionAt 0°-5° C. there are added 8 ml
  3. additionAfter the addition of 100 g
  4. extractionof sodium chloride, the separated oil is extracted with methylene chloride
  5. washThe organic phase is washed with a solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. dissolutionThe oily residue is dissolved in 200 ml
  9. customThe solution obtained
  10. temperatureis cooled in an ice-bath
  11. customcolorless crystals separating

Sources & evidence

ORD record
ord-b875ca15cf484b81bc755c762bb41638
Source dataset
uspto-grants-1976_12
Patent number
US03996374

Reaction notes

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