Imidazole → HCID 13588977, compound

HRID 1788683Notes

Reaction equation

HRID 1788683 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.[Na].[H-].[Na+]>CN(C)C=O>[N:23]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 24758Sodium hydrideHCID 5948562-(10-Bromodecyl)-1H-isoindole-1,3(2H)-dioneHCID 5360545Sodium

Product 1

HCID 13588977HCID 13588977, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 99.0 g amount of 2-(10-bromodecyl)-1H-isoindole-1,3(2H)-dione (prepared as described above) was dissolved in 300 ml of warm N,N-dimethylformamide with stirring. This solution was added to a stirred solution of 1H-imidazole, sodium salt (prepared by stirring a mixture of 20 g of imidazole and 14.0 g 50% sodium hydride in 500 ml of N,N-dimethylformamide at room temperature for 48 hours). The resulting mixture was heated on a steam bath for 14 hours, then taken to dryness in vacuo. The residue was partitioned between 500 ml of dichloromethane and 250 ml of water. The organic layer was washed with 250 ml of water, dried over magnesium sulfate and filter. The filtrate was evaporated in vacuo and gave 85.4 g of 2[10-(1H-imidazol-1-yl)decyl]-1H-isoindole-1,3(2H)dione as an oil which solidified on standing at room temperature.

Workup

  1. customprepared
  2. stirringby stirring
  3. temperatureThe resulting mixture was heated on a steam bath for 14 hours
  4. customThe residue was partitioned between 500 ml of dichloromethane and 250 ml of water
  5. washThe organic layer was washed with 250 ml of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfilter
  8. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c1284db6c5b14f14ad6b87eb7b078f36
Source dataset
uspto-grants-1987_08
Patent number
US04684654

Reaction notes

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