Sodium hydride → 1-Cyclopropylimidazolidin-2-one

HRID 2278967Notes

Reaction equation

HRID 2278967 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1>[CH:8]1([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 60638916HCID 60638916, compound

Product 1

HCID 539368821-Cyclopropylimidazolidin-2-oneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of 1-(2-chloroethyl)-3-cyclopropylurea (1.31 g, 8.06 mmol) in THF (40 mL) was treated with NaH (60% in mineral oil, 0.387 g, 9.67 mmol), stirred for 10 minutes, then warmed to RT and stirred for 6 h. The mixture was treated with satd. NH4Cl, the solids removed via filtration and washed with EtOAc. The filtrate was washed with brine, dried over Na2SO4 and concentrated to dryness to afford crude 1-cyclopropylimidazolidin-2-one (760 mg, 75%) which was used without further purification.

Workup

  1. stirringstirred for 6 h
  2. additionThe mixture was treated with satd
  3. customNH4Cl, the solids removed via filtration
  4. washwashed with EtOAc
  5. washThe filtrate was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b946a33d4cab406c8fa47952e3118f1f
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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