Benzoyl chloride → N,N'-{4-[3-(Diethylamino)propoxy]-1,3-phenylene}dibenzamide

HRID 1439160Notes

Reaction equation

HRID 1439160 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].O.O.O.[C:10]([O-])(=O)[CH3:11].[Na+].Cl.Cl.Cl.[CH2:18]([N:20]([CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][C:26]=1[NH2:32])[CH3:19].[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.O1CCOCC1>[CH2:33]([N:20]([CH2:18][CH3:19])[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:27][C:26]=1[NH:32][C:1](=[O:4])[C:11]1[CH:10]=[CH:27][CH:26]=[CH:25][CH:30]=1)[CH3:34]

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 21398316HCID 21398316, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 21398336N,N'-{4-[3-(Diethylamino)propoxy]-1,3-phenylene}dibenzamideYield 118.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of potassium carbonate (6.2 g), sodium acetate trihydrate (19 g), water (100 ml) and dioxane (100 ml) was added 1-(3'-diethylaminopropoxy)-2,4-diaminobenzene trihydrochloride (10.4 g) immediately followed by adding benzoyl chloride (13 g) while cooling with ice, and thereafter, the resulting mixture was stirred at room temperature for 2 hours. Then, after the addition of water (500 ml), the pH of the mixture was adjusted to 9 - 10 and the precipitated crystals were recovered by filtration. After washing the crystals with water, they were recrystallized twice from methanol-water to obtain 7.9 g of 1-(3'-diethylaminopropoxy)-2,4-bis(benzamido)-benzene having a melting point between 139° and 140° C.

Workup

  1. temperaturewhile cooling with ice
  2. filtrationthe precipitated crystals were recovered by filtration
  3. washAfter washing the crystals with water, they
  4. customwere recrystallized twice from methanol-water

Sources & evidence

ORD record
ord-2c7243936c4f4d0aa0a1c39c5c079065
Source dataset
uspto-grants-1977_11
Patent number
US04058523

Reaction notes

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