Tert-Butyl hypochlorite → 3-Chloro-4-(chloromethyl)-4-methyloxazolidin-2-one

HRID 1025919Notes

Reaction equation

HRID 1025919 reaction equation
[Cl:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.C(O[Cl:15])(C)(C)C>CO>[Cl:15][N:4]1[C:3]([CH2:2][Cl:1])([CH3:9])[CH2:7][O:6][C:5]1=[O:8]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

Product 1

HCID 569618563-Chloro-4-(chloromethyl)-4-methyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (13.39 g, 89.52 mmol) in MeOH (100 ml) was cooled to 0° C., and tert-butylhypochlorite (12.0 ml, 101 mmol) was added dropwise over 15 min. The solution was warmed to RT over 45 min, and concentrated in vacuo. The residue was crystallized by dissolution in ˜80 ml CH2Cl2 followed by careful layering of 60 ml hexanes to afford the title compound as white, fan-shaped crystals (12.31 g, 66.89 mmol, 75%). 1H NMR (CDCl3, 400 MHz) δ1.50 (s, 3H), 3.55 (d, J=12.0 Hz, 1H), 3.75 (d, J=12.0 Hz, 1H), 4.19 (d, J=8.8 Hz, 1H), 4.53 (d, J=8.4 Hz, 1H). 13C NMR (CDCl3, 100 MHz) δ 20.4, 46.7, 64.1, 155.7. LRMS (ESI/APCI): 225 [M+H+CH3CN]+, 191 [M+H−Cl+CH3CN]+, 184 [M+H]+, 150 [M+H−Cl]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was crystallized by dissolution in ˜80 ml CH2Cl2

Sources & evidence

ORD record
ord-eb14a690763c47919a647f204dc86a89
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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