4-Chlorobenzoyl chloride → HCID 13588922, compound

HRID 1589175Notes

Reaction equation

HRID 1589175 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:8][CH2:9][CH:10]([NH2:12])N)[CH:5]=[CH:6][N:7]=1)[CH3:2].[OH-].[Na+].[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C(Cl)Cl>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:12][CH2:10][CH2:9][CH2:8][N:4]2[CH:5]=[CH:6][N:7]=[C:3]2[CH2:1][CH3:2])=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium Hydroxide2×HCID 20248335HCID 20248335, compound

Product 1

HCID 13588922HCID 13588922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2.3 g. of 2-ethyl-1H-imidazole-1-propanediamine, 15 ml. of 2N sodium hydroxide and 150 ml. of methylene chloride was stirred at room temperature and 4.0 ml. of 4-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. The crystalline residue was washed onto a filter with ether and melted at 120°-122° C.

Workup

  1. additionA mixture of 2.3 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 crystalline residue was washed onto
  7. filtrationa filter with ether and melted at 120°-122° C.

Sources & evidence

ORD record
ord-99053fd4e5394a03a9e89c5ac47839d4
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

Loading…