Sodium hydride → HCID 15675475, compound

HRID 974016Notes

Reaction equation

HRID 974016 reaction equation
[CH2:1]([O:8][NH:9][C:10]([NH:12][CH2:13][CH2:14]Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>C1COCC1>[CH2:1]([O:8][N:9]1[CH2:14][CH2:13][NH:12][C:10]1=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 15675474HCID 15675474, compound

Product 1

HCID 15675475HCID 15675475, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of benzyloxyamine (36.63 g, 0.297 mol) in THF (250 ml) was added a solution of 2-chloroethyl isocyanate (25.4 ml, 1.0 equiv.) in THF (50 ml) over 20 minutes. The resulting cloudy solution was refluxed for 10 minutes, cooled and evaporated. Trituration of the residue with ether-hexane gave N-benzyloxy-N'-(2-chloroethyl)urea as a white solid (65.82 g, 97% yield), mp 67°-68° C. after recrystallization from hexane-ether. To a stirred solution of this urea (65.8 g, 0.287 mol) in the THF (500 ml) at room temperature was added sodium hydride (11.8 g of 60% dispersion in oil, 1.02 equiv.) in portions over 30 minutes. The cloudy solution was refluxed for 10 minutes, cooled and evaporated. To the resulting semi-solid was added 2% aqueous citric acid (60 ml) and hexane (250 ml). After vigorous agitation, the resulting solid was collected by filtration and washed with water and hexane, to give 1-benzyloxy-2-imidazolidinone as a tan solid (52.66 g, 93% yield), mp 64°-65° C. after recrystallization from water.

Workup

  1. customafter recrystallization from hexane-ether
  2. temperatureThe cloudy solution was refluxed for 10 minutes
  3. temperaturecooled
  4. customevaporated
  5. additionTo the resulting semi-solid was added 2% aqueous citric acid (60 ml) and hexane (250 ml)
  6. filtrationAfter vigorous agitation, the resulting solid was collected by filtration
  7. washwashed with water and hexane

Sources & evidence

ORD record
ord-3b3e8b6721f045208a6e27502ff155fc
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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