Tert-Butyl hypochlorite → 3-Chloro-4-(chloromethyl)-1,4-dimethylimidazolidin-2-one

HRID 1025925Notes

Reaction equation

HRID 1025925 reaction equation
[Cl:1][CH2:2][C:3]1([CH3:10])[CH2:7][N:6]([CH3:8])[C:5](=[O:9])[NH:4]1.C(O[Cl:16])(C)(C)C>CO>[Cl:16][N:4]1[C:3]([CH2:2][Cl:1])([CH3:10])[CH2:7][N:6]([CH3:8])[C:5]1=[O:9]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 867145864-(Chloromethyl)-1,4-dimethylimidazolidin-2-one

Product 1

HCID 867145873-Chloro-4-(chloromethyl)-1,4-dimethylimidazolidin-2-oneYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(chloromethyl)-1,4-dimethylimidazolidin-2-one (204 mg, 1.25 mmol) in MeOH (2.5 ml) was cooled to 0° C. tert-Butylhypochlorite (177 ul, 1.57 mmol) was added. The resulting solution was stirred for 60 min, during which time a white precipitate formed. The reaction mixture was concentrated under reduced pressure to half its initial volume and the solid was collected on a glass fritted filter and washed with water to give 168 mg of desired product (69% yield). 1H NMR (400 MHz, CDCl3) δ1.48 (s, 3H), 2.90 (s, 3H), 3.21-3.23 (d, J=8.8 Hz, 1H), 3.52-3.54 (d, J=8.9 Hz, 1H), 3.59-3.67 (q, J=11.1 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ 19.9, 31.7, 47.6, 54.5, 63.1, 158.7. LRMS (ESI/APCI): 197 [M+H]+.

Workup

  1. additionwas added
  2. customformed
  3. concentrationThe reaction mixture was concentrated under reduced pressure to half its initial volume
  4. customthe solid was collected on a glass fritted filter
  5. washwashed with water

Sources & evidence

ORD record
ord-29efd968a3784c52b457c84262e6ce39
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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