1-Bromohexane → HCID 4685260, compound

HRID 244962Notes

Reaction equation

HRID 244962 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[H-].[Na+].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CN(C)C=O.[I-].[Na+]>[CH2:12]([O:1][N:2]1[C:6](=[O:7])[C:5]2[C:4](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:3]1=[O:8])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 4685260HCID 4685260, compoundYield 261.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

3.0 g (18 mmol) of N-hydroxysuccinimide was dissolved in 30 mL of N,N-dimethylformamide, mixed with 0.81 g (20 mmol) of 60 wt % sodium hydride (dispersed in mineral oil) under cooling with ice and stirred at room temperature for 30 minutes. After the stirring, 2.8 mL (20 mmol) of bromohexane and 35 mg (0.23 mmol) of sodium iodide were added dropwise successively under cooling with ice, and the reaction mixture was stirred at 70° C. for 20 hours. After completion of the reaction, the reaction mixture was poured into ice-cold water, and the solid precipitated in the reaction mixture was collected by filtration and dried to give 5.82 g of the desired product as a white solid.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe reaction mixture was stirred at 70° C. for 20 hours
  4. customAfter completion of the reaction
  5. additionthe reaction mixture was poured into ice-cold water
  6. customthe solid precipitated in the reaction mixture
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-9699b44c68014b4098d704db8268b068
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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