1,4-Dichlorobutane → HCID 20469801, compound

HRID 1388319Notes

Reaction equation

HRID 1388319 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13]Cl>CN(C)C=O>[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][N:5]1[CH2:6][CH2:7][O:3][C:4]1=[O:8]

Participants

5

Reactant 3

HCID 80591,4-DichlorobutaneHCID 24758Sodium hydrideHCID 739492-Oxazolidinone

Product 1

HCID 20469801HCID 20469801, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Piper et al. [J. Het. Chem. 4, p. 298 (1967)], sodium hydride (4.8 g of 50% dispersion in oil, 0.1 mole) was washed with pentane and suspended in 20 ml of dimethylformamide. A solution of 2-oxazolidinone (8.7 g, 0.10 mole) and 1,4-dichlorobutane (66 g, 0.52 mole) in 100 ml of dimethylformamide was then added dropwise over 30 minutes, maintaining the reaction temperature at 25°-30° C. The reaction was stirred for 18 hours at ambient temperature, then evaporated to an oil, and the oil taken up in ethyl acetate, treated with activated carbon, filtered over diatomaceous earth, and reevaporated in vacuo to yield the title product as an oil [16.5 g, contaminated with mineral oil from incompletely washed sodium hydride; pnmr/CDCl3 /delta: 0.67-1.0 and 1.03-1.4 (mineral oil), 1.4-1.83 (m, 4H), 3.03-3.72 (m, 6H), 4.10-4.43 (t, 2H)].

Workup

  1. washwas washed with pentane
  2. temperaturemaintaining the reaction temperature at 25°-30° C
  3. customevaporated to an oil
  4. additiontreated with activated carbon
  5. filtrationfiltered over diatomaceous earth
  6. customreevaporated in vacuo

Sources & evidence

ORD record
ord-4cf6a6785baa4d16b7fb380373f5e689
Source dataset
uspto-grants-1984_02
Patent number
US04431646

Reaction notes

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