Hydroxyethyl imidazolidinone → HCID 56966448, compound

HRID 1770770Notes

Reaction equation

HRID 1770770 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].C(O[Cl:15])(C)(C)C>CO>[Cl:15][N:6]1[CH2:7][CH2:8][N:4]([CH2:3][CH2:2][OH:1])[C:5]1=[O:9]

Participants

4

Reactant 2

HCID 77290Hydroxyethyl imidazolidinoneHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 56966448HCID 56966448, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(2-hydroxyethyl)imidazolidin-2-one (418 mg, 3.2 mmol) in MeOH (6 ml) was cooled to 0° C. tert-Butylhypochlorite (450 ul, 4 mmol) was added. The resulting solution was stirred for 90 min and then concentrated under reduced pressure. The crude material was purified by column chromatography (0 to 12% methanol in dichloromethane) to give a white solid (317 mg, 1.93 mmol, 60%). 1H NMR (400 MHz, D2O) δ 3.28-3.31 (t, J=5.3 Hz, 2H), 3.47-3.51 (m, 2H), 3.56-3.59 (m, 2H), 3.62-3.64 (t, J=5.3 Hz, 2H). 13C NMR (100 MHz, D2O) δ 43.31, 46.6, 51.9, 58.3, 163.9. LRMS (ESI/APCI) m/z 165 [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-59667cb5d17c48e087d06d9851d10d30
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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