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

HRID 1589174Notes

Reaction equation

HRID 1589174 reaction equation
Cl.Cl.[N:3]1([CH2:8][CH2:9][CH2:10][NH2:11])[CH:7]=[CH:6][N:5]=[CH:4]1.[OH-].[Na+].[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19]>C(Cl)Cl>[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH:11][CH2:10][CH2:9][CH2:8][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:19]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 69252Benzoyl chloride, 3-chloro-HCID 122509693-(Imidazole-1-yl)-propylamine Dihydrochloride

Product 1

HCID 28482203-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6.0 g. of 1H-imidazole-1-propanamine dihydrochloride, 45 ml. of 2N sodium hydroxide and 150 ml. of methylene chloride was stirred at room temperature and 3.9 ml. of 3-chlorobenzoyl chloride was added. The reaction mixture was stirred for 18 hours, then methylene chloride and 15 ml. of 1N sodium hydroxide were added and the layers were separated. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to remove the solvent. The residue was triturated with diethyl ether and the crystalline product recovered by filtration and recrystallized from ethanol, giving the desired product, m.p. 125°-127° C.

Workup

  1. additionA mixture of 6.0 g
  2. customthe layers were separated
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto remove the solvent
  7. customThe residue was triturated with diethyl ether
  8. filtrationthe crystalline product recovered by filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e7a99a1e55744f3d8b8b83b92d1c4af8
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

Loading…