Sodium hydride → 1-Tert-butylimidazolidin-2-one

HRID 2278960Notes

Reaction equation

HRID 2278960 reaction equation
[C:1]([NH:5][C:6]([NH:8][CH2:9][CH2:10]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>C1COCC1>[C:1]([N:5]1[CH2:10][CH2:9][NH:8][C:6]1=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 2941631-Tert-butyl-3-(2-chloroethyl)urea

Product 1

HCID 27952311-Tert-butylimidazolidin-2-oneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of 1-(tert-butyl)-3-(2-chloroethyl)urea (2.00 g, 11.19 mmol) in THF (20 mL) was treated with NaH (60% in mineral oil, 0.800 g, 33.3 mmol), stirred at RT for 1 h, then heated at 65° C. overnight. The mixture was cooled to RT, 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-(tert-butyl)imidazolidin-2-one (1.19 g, 75%). MS (ESI) m/z: 143.1 (M+H+).

Workup

  1. temperatureheated at 65° C. overnight
  2. temperatureThe mixture was cooled to RT
  3. concentrationconcentrated to dryness
  4. additiontreated with satd
  5. extractionNH4Cl, extracted with EtOAc (3×)
  6. dry with materialthe combined organics were dried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d179fba08b674fd193dbf8c42a3f87dd
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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