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

HRID 1770769Notes

Reaction equation

HRID 1770769 reaction equation
[OH: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][OH:1])([CH3:10])[CH2:7][N:6]([CH3:8])[C:5]1=[O:9]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 675087194-(Hydroxymethyl)-1,4-dimethylimidazolidin-2-one

Product 1

HCID 545854373-Chloro-4-(hydroxymethyl)-1,4-dimethylimidazolidin-2-oneYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(hydroxymethyl)-1,4-dimethylimidazolidin-2-one (250 mg, 1.72 mmol) in methanol (2.5 ml) was cooled to 0° C. tert-Butylhypochlorite (236 ul, 2.1 mmol) was added. The resulting solution was stirred for 30 minutes, then concentrated under reduced pressure to a crude residue. The crude material was purified by column chromatography (1 to 12% methanol in dichloromethane) to give the desired product as a white solid (168 mg, 0.941 mmol, 54%). 1H NMR (400 MHz, D2O) δ 1.16 (s, 3H), 2.74 (s, 3H), 3.25-3.27 (d, J=9.2 Hz, 1H), 3.38-3.41 (d, J=12.6 Hz, 1H), 3.47-3.49 (d, J=9.2 Hz, 2H), 3.64-3.67 (d, J=12.6 Hz, 1H). 13C NMR (100 MHz, D2O) δ 18.1, 30.8, 53.2, 62.8, 64.5, 161.6. LRMS (ESI/APCI) m/z 179 [M+H]+.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure to a crude residue
  3. customThe crude material was purified by column chromatography (1 to 12% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d1a9b630d9464153ad0213447bf91363
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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