Tert-Butyl hypochlorite → HCID 56966445, compound

HRID 1770765Notes

Reaction equation

HRID 1770765 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]([CH3:15])([CH3:14])[NH:10][C:9]1([CH3:17])[CH3:16].C(O[Cl:23])(C)(C)C>CO>[Cl:23][N:10]1[C:11]([CH3:15])([CH3:14])[C:12](=[O:13])[N:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:9]1([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67508103HCID 67508103, compound

Product 1

HCID 56966445HCID 56966445, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(2-(2-methoxyethoxy)ethyl)-2,2,5,5-tetramethyl-imidazolidin-4-one (715 mg, 2.9 mmol) in methanol (7 ml) was cooled to 0° C. tert-Butylhypochlorite (393 ul, 3.5 mmol) was added. The resulting solution was stirred for 30 minutes, and then concentrated under reduced pressure. The crude material was purified by column chromatography (0 to 12% methanol in dichloromethane) to give the title compound as a clear liquid (666 mg, 2.39 mmol, 82%). 1H NMR (400 MHz, D2O) δ 1.26 (s, 6H), 1.43 (s, 6H), 3.27 (s, 3H), 3.44-3.46 (m, 2H), 3.49-3.51 (m, 2H), 3.57-3.63 (m, 4H). 13C NMR (100 MHz, D2O) δ 22.5, 24.0, 40.1, 57.9, 66.0, 67.6, 69.4, 71.0, 83.7, 175.0. LRMS (ESI/APCI) m/z 279 [M+H]+.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by column chromatography (0 to 12% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6cff35f71eb44997929e5044b3bfde61
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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