Sodium Hydroxide → 2-butyl-3,5-dihydro-4H-imidazol-4-one

HRID 1452072

Reaction equation

HRID 1452072 reaction equation
Cl.C[O:3][C:4](=O)[CH2:5][NH2:6].[OH-].[Na+].CO[C:12](=[NH:17])[CH2:13][CH2:14][CH2:15][CH3:16]>CO.ClC1C=CC=CC=1>[CH2:13]([C:12]1[NH:17][C:4](=[O:3])[CH2:5][N:6]=1)[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 122755Glycine methyl ester hydrochlorideHCID 5743466Methyl pentanimidate

Product 1

HCID 109096542-butyl-3,5-dihydro-4H-imidazol-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7964ChlorobenzeneSolvent2×

Procedure

31.71 g (0.25 mol) of glycine methyl ester hydrochloride was added to a solution of 10.1 g (0.25 mol) of sodium hydroxide in methanol at 0° C. After 15 minutes, 126.5 g of a 22.8 percent solution of pentanimidic acid methyl ester in chlorobenzene was instilled for 5 minutes to a white suspension. The light yellow suspension was stirred for 4 hours at room temperature and diluted with chlorobenzene (100 ml). The methanol was distilled off at a temperature of 26° C. and a pressure of 30 to 50 mbar, and the orange suspension was diluted with methylene chloride (100 ml) and then filtered. After removal of the solvent from the filtrate, 34.08 g (97 percent) of the title compound (content >95 percent, according to GC and 1H-NMR) was obtained.

Workup

  1. distillationThe methanol was distilled off at a temperature of 26° C.
  2. additiona pressure of 30 to 50 mbar, and the orange suspension was diluted with methylene chloride (100 ml)
  3. filtrationfiltered
  4. customAfter removal of the solvent from the filtrate

Sources & evidence

ORD record
ord-8615f55fe1f44e9788d2026afdffc2f5
Source dataset
uspto-grants-1997_02
Patent number
US05606072

Linked notes

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