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

HRID 1589179Notes

Reaction equation

HRID 1589179 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+].[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>C(Cl)Cl>[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:15][CH2:14][CH2:13][CH2:12][N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[CH:9]2)=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 685154-Bromobenzoyl chlorideHCID 135889123-(4-Phenyl-1H-imidazol-1-yl)propan-1-amine

Product 1

HCID 135889214-Bromo-N-[3-(4-phenyl-1H-imidazol-1-yl)propyl]benzamide

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 2.2 g. of 4-bromobenzoyl 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 ether, giving the desired product, m.p. 132°-135° 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 ether

Sources & evidence

ORD record
ord-14ba947b417f4cf19189d66d73aa7c44
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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