Dimethylformamide → 2-{2-[2-(2-Methoxyethoxy)ethoxy]ethyl}-1H-isoindole-1,3(2H)-dione

HRID 1449593Notes

Reaction equation

HRID 1449593 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH:21](I)[CH3:22].CN(C)C=O>C(OCC)(=O)C>[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 233521122-Methoxyethoxyethoxy-1-iodoethaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 572064612-{2-[2-(2-Methoxyethoxy)ethoxy]ethyl}-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.3 g of potassium phthalimide, 2-methoxyethoxyethoxy-1-iodoethane and 5 ml of dimethylformamide were fed into a 100 ml short-neck flask provided with a reflux condenser. The resultant mixture was heated at 90° c. for 3 hours. 100 ml of ethyl acetate was added thereto and the resultant mixture was cooled to room temperature. White precipitates thus obtained were suction-filtered, and the filtrate was washed with 100 ml of water. The obtained ethyl acetate layer was dried over magnesium sulfate, and ethyl acetate was distilled off under reduced pressure to obtain the intended compound.

Workup

  1. customprovided with a reflux condenser
  2. customWhite precipitates thus
  3. customobtained
  4. filtrationwere suction-filtered
  5. washthe filtrate was washed with 100 ml of water
  6. dry with materialThe obtained ethyl acetate layer was dried over magnesium sulfate, and ethyl acetate
  7. distillationwas distilled off under reduced pressure
  8. customto obtain the intended compound

Sources & evidence

ORD record
ord-b6cfd3f61fe945c0a3fde048ea7bb1b4
Source dataset
uspto-grants-1997_02
Patent number
US05599825

Reaction notes

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