1,6-Dibromohexane → HCID 20469869, compound

HRID 1388320Notes

Reaction equation

HRID 1388320 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][Br:10].[O:11]1[CH2:15][CH2:14][NH:13][C:12]1=[O:16]>CN(C)C=O>[Br:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:13]1[CH2:14][CH2:15][O:11][C:12]1=[O:16]

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 739492-Oxazolidinone

Product 1

HCID 20469869HCID 20469869, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the procedure of Example 1, sodium hydride (3.85 g of 50% dispersion in oil, 0.0804 mole), 1,6-dibromohexane (24.5 ml, 0.16 mole) and 2-oxazolidinone (7.0 g, 0.0804 mole) in dimethylformamide (180 ml total) were reacted and the reaction mixture concentrated to one tenth volume. Hexane (200 ml) was added, salts were removed by filtration, and the heavy, oily layer separated from the filtrate. This heavy layer was chromatographed on silica gel with ethyl acetate as eluant and tlc monitoring. Clean product-containing fractions were combined and evaporated to yield the title product as an oil [1.59 g; Rf 0.5 (ethyl acetate)].

Workup

  1. concentrationthe reaction mixture concentrated to one tenth volume
  2. additionHexane (200 ml) was added
  3. customsalts were removed by filtration
  4. customthe heavy, oily layer separated from the filtrate
  5. customThis heavy layer was chromatographed on silica gel with ethyl acetate as eluant
  6. additionClean product-containing fractions
  7. customevaporated

Sources & evidence

ORD record
ord-b115d76cda624581af9cc8f0fa4285fd
Source dataset
uspto-grants-1984_02
Patent number
US04431646

Reaction notes

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