Methanol → 5-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one

HRID 660866Notes

Reaction equation

HRID 660866 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][NH:10][C:11]([NH:13][CH:14]2[CH2:16][CH2:15]2)=[O:12])=[CH:4][CH:3]=1.CO>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]([CH:14]3[CH2:16][CH2:15]3)[C:11](=[O:12])[NH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 58011668N-[2-(4-chlorophenyl)-2-oxoethyl]-N'-cyclopropylurea

Product 1

HCID 580118325-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1525 mg (6.035 mmol) of N-[2-(4-chlorophenyl)-2-oxoethyl]-N′-cyclopropylurea from Example 113A are suspended in 25 ml of concentrated hydrochloric acid, treated with 25 ml methanol and stirred for one hour at room temperature. The reaction mixture is evaporated to dryness and the residue purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 100:1, then 50:1). 1300 mg (90% of theory) of the target compound are obtained.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue purified by flash chromatography on silica gel (eluent
  3. custom1300 mg (90% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-ddbf949385824259a9de6526d3fe0f94
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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