Sodium hydride → 1-(Propan-2-yl)imidazolidin-2-one

HRID 2278962Notes

Reaction equation

HRID 2278962 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]([CH3:10])[CH3:9])=[O:6].[H-].[Na+]>C1COCC1>[CH:8]([N:7]1[CH2:2][CH2:3][NH:4][C:5]1=[O:6])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 3485544883805-52-5

Product 1

HCID 217190151-(Propan-2-yl)imidazolidin-2-oneYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. suspension of 1-(2-chloroethyl)-3-isopropylurea (6.00 g, 36.4 mmol) in THF (60 mL) was treated with NaH (60% in mineral oil, 2.50 g, 104 mmol) and stirred at RT overnight. The mixture was concentrated to dryness, treated with satd. NH4Cl, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 1-isopropylimidazolidin-2-one (3.21 g, 69%) as a waxy solid. MS (ESI) m/z: 129.1 (M+H+).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiontreated with satd
  3. extractionNH4Cl, extracted with EtOAc (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c8ebc16c427d48f698834a279f7a3c35
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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