4,4-bis(chloromethyl)-1,3-oxazolidin-2-one → HCID 53359811, compound

HRID 1025932Notes

Reaction equation

HRID 1025932 reaction equation
[Cl:1][CH2:2][C:3]1([CH2:9][Cl:10])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.C(O[Cl:16])(C)(C)C>CO>[Cl:16][N:4]1[C:3]([CH2:9][Cl:10])([CH2:2][Cl:1])[CH2:7][O:6][C:5]1=[O:8]

Participants

4

Reactant 2

HCID 2801944,4-bis(chloromethyl)-1,3-oxazolidin-2-oneHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 53359811HCID 53359811, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4,4-bis(chloromethyl)oxazolidin-2-one (1.11 g, 6.03 mmol) in MeOH (10 ml) was added tert-butylhypochlorite (1.0 ml, 8.4 mmol). The solution was stirred for 1 h, concentrated in vacuo, and the residue purified by flash chromatography (30% to 80% EtOAc in hexanes) to afford the title compound as a white solid (1.04 g, 4.76 mmol, 79%). 1H NMR (CDCl3, 400 MHz) δ 3.78 (d, J=12.0 Hz, 2H), 3.84 (d, J=12.4 Hz, 2H), 4.55 (s, 2H). LRMS (ESI/APCI): 228 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by flash chromatography (30% to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bc60e22adff445699da6c55b5dad6aec
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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