Dimethylformamide → 1H-Isoindole, 2,3-dihydro-5,6-dimethoxy-2-[(4-methylphenyl)sulfonyl]-

HRID 704452Notes

Reaction equation

HRID 704452 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][C:25]1[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[CH:29][C:30]=1[CH2:31]Cl>O>[CH3:36][O:35][C:27]1[CH:26]=[C:25]2[C:30](=[CH:29][C:28]=1[O:33][CH3:34])[CH2:31][N:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])[CH2:24]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6269P-ToluenesulfonamideHCID 11430Potassium CarbonateHCID 109444001,2-Bis(chloromethyl)-4,5-dimethoxybenzene

Product 1

HCID 100881951H-Isoindole, 2,3-dihydro-5,6-dimethoxy-2-[(4-methylphenyl)sulfonyl]-Yield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.89 g (11 mmol) of p-toluenesulfonamide was added to 20 ml of N,N-dimethylformamide, and 3.3 g (24 mmol) of pulverised potassium carbonate and 2.0 g (8.5 mmol) of 4,5-bischloromethyl veratrol were added thereto at room temperature under stirring. The mixture was stirred at room temperature for 20 hours, and after an addition of 40 ml of water, extracted with methylene chloride. The extract was washed with water, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the crystalline residue was washed with diisopropyl ether to obtain 2.7 g (yield: 95.2%) of the above identified compound.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at room temperature for 20 hours
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washthe crystalline residue was washed with diisopropyl ether
  8. customto obtain 2.7 g (yield: 95.2%) of the

Sources & evidence

ORD record
ord-2e432545c2b04e81ab2093d4b30a8040
Source dataset
uspto-grants-1991_01
Patent number
US04987235

Reaction notes

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