Ethanol → HCID 22930233, compound

HRID 968809Notes

Reaction equation

HRID 968809 reaction equation
[CH2:1]([CH:3]([CH2:14][CH3:15])[CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[N+:11]([O-])=O)[CH3:2].C(O)C>[C].[Pd].C(OCC)(=O)C>[CH2:14]([CH:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH2:11])[CH3:15]

Participants

5

Reactant 2

HCID 702EthanolHCID 22930226HCID 22930226, compound

Product 1

HCID 22930233HCID 22930233, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the 1-(3-ethylpentyl)-2-nitro-1H-imidazole (370 mg) and 10% palladium-carbon (200 mg) in an ethanol (5 ml)-ethyl acetate (5 ml) mixture was stirred at room temperature and normal pressure for 20 hours under a hydrogen stream. After filtering the reaction mixture through celite, it was washed with ethyl acetate-methanol. The filtrate was distilled off under reduced pressure to yield a crude product of 1-(3-ethylpentyl)-1H-2-imidazoleamine (305 mg) as a light yellow solid. A solution of the 1-(3-ethylpentyl)-1H-2-imidazoleamine (305 mg, 1.68 mmol) and 2-bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]-1-ethanone (660 mg, 2.02 mmol) in methanol (20 ml) was heated at 60° C. for 3 hours. The reaction mixture was distilled under reduced pressure, and the obtained crude product was recrystallized from ethyl acetate. After washing the crystals with diethyl ether, they were dried to yield the target compound (700 mg) as a colorless amorphous solid.

Workup

  1. filtrationAfter filtering the reaction mixture through celite, it
  2. washwas washed with ethyl acetate-methanol
  3. distillationThe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-05338ed483b44507ae29f82b1cc89fd6
Source dataset
uspto-grants-2007_12
Patent number
US07304083B2

Reaction notes

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