Sodium Chloride → 1-Cyclohexyl-2-imidazolidinone

HRID 2278938Notes

Reaction equation

HRID 2278938 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:9][CH2:10][N:11]=[C:12]=[O:13].[H-].[Na+].[NH4+].[Cl-].[Na+].[Cl-]>C1COCC1>[CH:1]1([N:7]2[CH2:9][CH2:10][NH:11][C:12]2=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 7965CyclohexylamineHCID 160352-Chloroethyl isocyanateHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 5803521-Cyclohexyl-2-imidazolidinoneYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclohexylamine (1.00 g, 10.08 mmol) and 2-chloro ethylisocyanate (1.064 g, 10.08 mmol) in THF (30 mL) was stirred at RT for 4 h, treated with sodium hydride (60% in mineral oil, 0.403 g, 10.08 mmol) and stirred at RT for 16 h. The mixture was poured into satd. NH4Cl, treated with solid NaCl until saturated, extracted with THF (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The material was suspended in 30% EtOAc/Hex, stirred and the resulting solid collected via filtration to afford 1-cyclohexylimidazolidin-2-one (650 mg, 38%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.14 (s, 1 H), 3.46-3.37 (m, 1 H), 3.27-3.21 (m, 2 H), 3.19-3.13 (m, 2 H), 1.75-1.68 (m, 2 H), 1.60-1.50 (m, 3 H), 1.37-1.18 (m, 4 H), 1.09-0.98 (m, 1 H).

Workup

  1. additionThe mixture was poured into satd
  2. extractionextracted with THF (2×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. stirringstirred
  7. filtrationthe resulting solid collected via filtration

Sources & evidence

ORD record
ord-1cd6f05de3a2453b8a2ec321cfb1bcc8
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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