Tert-Butyl hypochlorite → HCID 86665539, compound

HRID 1770737Notes

Reaction equation

HRID 1770737 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][S:11]([CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[NH:18][C:17]1=[O:24])(=[O:13])=[O:12].C(O[Cl:30])(C)(C)C>CO>[Cl:30][N:18]1[C:19]([CH3:22])([CH3:23])[C:20](=[O:21])[N:16]([CH2:15][CH2:14][S:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:13])=[O:12])[C:17]1=[O:24]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67508349HCID 67508349, compound

Product 1

HCID 86665539HCID 86665539, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(2-((2-(2-(2-methoxyethoxy)ethoxy)ethyl)sulfonyl)ethyl)-5,5-dimethylimidazolidine-2,4-dione (1.9 g, 5.2 mmol) in methanol (10 ml) was cooled to 0° C. tert-Butylhypochlorite (613 ul, 5.45 mmol) was added. The resulting solution was stirred for 3 hours at 0° C., and then concentrated under reduced pressure. The crude material was purified by column chromatography, eluting from silica gel with a gradient of 5-12% methanol in dichloromethane to give 1.1 g of a clear oil. 1H NMR (D2O, 400 MHz) δ 1.39 (s, 6H), 3.28 (s, 3H), 3.43-3.47 (t, J=5.4 Hz, 2H), 3.51-3.61 (m, 10H) 3.85-3.88 (t, 5.2 Hz, 2H), 4.02-4.05 (m, 2H). LRMS (ESI/APCI) m/z 401 [M+H]+.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by column chromatography
  4. washeluting from silica gel with a gradient of 5-12% methanol in dichloromethane

Sources & evidence

ORD record
ord-1c79dd36fb4e4cbcbfacdf148dfc21d5
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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