Sodium Bromide → HCID 86714590, compound

HRID 1025929Notes

Reaction equation

HRID 1025929 reaction equation
Cl[CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.[Br-:10].[Na+]>CN(C=O)C>[Br:10][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1

Participants

4

Reactant 2

HCID 253881Sodium BromideHCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

Product 1

HCID 86714590HCID 86714590, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (1.49 g, 9.96 mmol) in DMF (100 ml) was added sodium bromide (11.02 g, 107 mmol), and the suspension heated to 80° C. for 6 h. The suspension was concentrated in vacuo and the residue purified by flash chromatography (30% to 60% ethyl acetate in hexanes) to give the title compound as a white solid (1.33 g, 6.86 mmol, 66%). 1H NMR (CDCl3, 400 MHz) δ 1.54 (s, 3H), 3.47 (s, 2H), 4.14 (d, J=9.2 Hz, 1H), 4.35 (d, J=8.8 Hz, 1H), 6.24 (br s, 1H). LRMS (ESI/APCI): 194 [M+H]+.

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. customthe residue purified by flash chromatography (30% to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-754682a2887a4d5bb880f33d8419dba6
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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