Sodium Hydroxide → N-[3-(4-phenyl-1H-imidazol-1-yl)propyl]-2-furanecarboxamide

HRID 1154335Notes

Reaction equation

HRID 1154335 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][N:10]([CH2:12][CH2:13][CH2:14][NH2:15])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24]>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([CH2:12][CH2:13][CH2:14][NH:15][C:23]([C:19]3[O:18][CH:22]=[CH:21][CH:20]=3)=[O:24])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 682422-Furancarbonyl chlorideHCID 135889123-(4-Phenyl-1H-imidazol-1-yl)propan-1-amine

Product 1

HCID 13371090N-[3-(4-phenyl-1H-imidazol-1-yl)propyl]-2-furanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2.0 g. of 4-phenyl-1H-imidazole-1-propanamine, 50 ml. of methylenechloride and 10 ml. of 1N sodium hydroxide was stirred and 2.0 ml. of 2-furoyl chloride was added. The mixture was stirred for eighteen hours, methylene chloride was added and the layers were separated. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue was washed onto a filter with diethyl ether, giving the desired product, m.p. 120°-122° C.

Workup

  1. additionA mixture of 2.0 g
  2. customthe layers were separated
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. washThe residue was washed onto
  7. filtrationa filter with diethyl ether

Sources & evidence

ORD record
ord-3c253e52698e49da9182f65322d084c1
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Reaction notes

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