Isocyanatocyclopropane → Ethyl [4-(4-chlorophenyl)-3-cyclopropyl-5-methyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

HRID 660872Notes

Reaction equation

HRID 660872 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][NH:6][CH:7]([CH3:17])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=O)[CH3:2].[CH:19]1([N:22]=[C:23]=[O:24])[CH2:21][CH2:20]1>O1CCCC1>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:7]([CH3:17])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[N:22]([CH:19]2[CH2:21][CH2:20]2)[C:23]1=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 637659IsocyanatocyclopropaneHCID 57455730N-[2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-glycine ethyl ester

Product 1

HCID 58012249Ethyl [4-(4-chlorophenyl)-3-cyclopropyl-5-methyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

355 mg (1.32 mmol) of N-[2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-glycine ethyl ester from Example 117A are placed in 5 ml tetrahydrofuran, treated with 109 mg (1.32 mmol) of cyclopropyl isocyanate and stirred overnight at room temperature. The reaction mixture is evaporated and the residue purified by flash chromatography on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 200:1→100:1). 425 mg (91% of theory) of the target compound are thus obtained.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue purified by flash chromatography on silica gel (eluent
  3. custom425 mg (91% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-11ca6f622d1c4fcfa245cc9680d0d1a1
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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