Water → HCID 17986393, compound

HRID 970428Notes

Reaction equation

HRID 970428 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].Br[CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32].O>CN(C=O)C>[N+:7]([C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[O:16][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32])([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 17986393HCID 17986393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.67 g (70 mmol) of potassium carbonate is added to a solution of 6.96 g (50 mmol) of 3-nitrophenol in 500 ml DMF, and then it is stirred for 10 minutes at room temperature. It is mixed with 14.1 g (50 mmol) of 2-(4-bromo-butyl)-isoindole-1,3-dione and stirred for 4 hours at 60° C. After cooling, it is mixed with water and extracted with ethyl acetate. The combined organic phases are dried (MgSO4), filtered and concentrated by evaporation. 17.2 g (50 mmol, corresponding to 100% of theory) of the product is obtained.

Workup

  1. stirringstirred for 4 hours at 60° C
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. custom17.2 g (50 mmol, corresponding to 100% of theory) of the product is obtained

Sources & evidence

ORD record
ord-4fc3d80fd1fe436f9effcade7fdf3f52
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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