Tert-Butyl hypochlorite → HCID 56966447, compound

HRID 1770753Notes

Reaction equation

HRID 1770753 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[NH:7][C:6]1([CH3:14])[CH3:13].[Cl:15]OC(C)(C)C>CO>[Cl:15][N:7]1[C:8]([CH3:12])([CH3:11])[C:9](=[O:10])[N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:6]1([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67508811HCID 67508811, compound

Product 1

HCID 56966447HCID 56966447, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(2-methoxyethyl)-2,2,5,5-tetramethylimidazolidin-4-one (0.70 g, 3.5 mmol) in methanol (10 mL) was cooled in ice water for 10 minutes, before neat tert-butyl hypochlorite (0.59 mL, 5.25 mmol, 1.5 equiv.) was added in one portion. High pressure liquid chromatography-mass spectroscopy analysis after 5 minutes showed all starting amine had been consumed. After 20 minutes, the mixture was concentrated in vacuo to an oil. The oil absorbed was on silica (2.5 g) and was purified by silica gel flash chromatography (0-4% methanol in dichloromethane) afforded the N-chloro-imidazolidin-4-one as a colorless oil (0.78 g, 95%). 1H NMR (400 MHz, CDCl3) δ 3.55 (t, J=5.8 Hz, 2H), 3.44 (t, J=6.4 Hz, 2H), 3.36 (s, 3H), 1.46 (s, 6H), 1.36 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 172.8, 82.0, 70.1, 65.3, 58.8, 40.5, 25.1, 23.5; LRMS (ESI/APCI) m/z 235 [M+H]+.

Workup

  1. additionwas added in one portion
  2. customall starting amine had been consumed
  3. waitAfter 20 minutes
  4. concentrationthe mixture was concentrated in vacuo to an oil
  5. customThe oil absorbed
  6. customwas purified by silica gel flash chromatography (0-4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7ee1eca6d35e4b0bae120a84c83e33af
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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