1,3-Dichloropropane → 3-(3-Chloropropyl)-2-oxazolidinone

HRID 1682440Notes

Reaction equation

HRID 1682440 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]Cl>CN(C=O)C>[Cl:9][CH2:10][CH2:11][CH2:12][N:5]1[CH2:6][CH2:7][O:3][C:4]1=[O:8]

Participants

5

Reactant 3

HCID 88811,3-DichloropropaneHCID 24758Sodium hydrideHCID 739492-Oxazolidinone

Product 1

HCID 133549643-(3-Chloropropyl)-2-oxazolidinoneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mechanically stirred, room temperature suspension of NaH (0.305 mole, hexane washed) in 50 mL of DMF under N2, was added 2-oxazolidinone (0.287 mole) portion wise. After stirring the resulting gelatinous mixture overnight, 1,3-dichloropropane (0.643 mole) was added and the mixture stirred 4 days at room temperature. The volatiles were then removed in vacuo and the resulting white residue taken up in CH2Cl2 and washed with H2O and brine, and dried over MgSO4. After filtration, the material was passed through a short column (SiO2 : EtOAc/Hex) to give (XVI) as a clear oil in 95% yield: 1H NMR (CDCl3) δ4.22 (t, 2H, J=6.6 Hz), 3.47 (m, 4H), 3.24 (t, 2H, J=7.0 Hz), and 1.98 (p, 2H, J=6.5 Hz); 13C NMR (CDCl3) δ158.5, 61.8, 45.0, 42.0, 41.8, and 30.2. Anal. Calcd for C6H10ClNO2 : C, 44.05; H, 6.16; N, 8.56. Found: 41.17; H, 5.77; N, 8.26.

Workup

  1. additionwas added
  2. stirringthe mixture stirred 4 days at room temperature
  3. customThe volatiles were then removed in vacuo
  4. washwashed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration

Sources & evidence

ORD record
ord-788db18b2306470180da7649f229ee92
Source dataset
uspto-grants-1997_06
Patent number
US05635503

Reaction notes

Loading…