Water → N,N'-bis(4-diethylaminobenzoyl)ethylenediamine

HRID 544244Notes

Reaction equation

HRID 544244 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH2:5]([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])[CH3:6].[CH2:12]([N:14]([CH2:24][CH3:25])[C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)[CH3:13].[OH2:26]>C(Cl)(Cl)Cl>[CH2:5]([N:7]([CH2:10][CH3:11])[C:8]1[CH:16]=[CH:17][C:18]([C:22]([NH:3][CH2:2][CH2:1][NH:4][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:15]([N:14]([CH2:24][CH3:25])[CH2:12][CH3:13])=[CH:16][CH:17]=2)=[O:26])=[CH:19][CH:9]=1)[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 8471TriethylamineHCID 127070214-(Diethylamino)benzoyl chloride

Product 1

HCID 13286641N,N'-bis(4-diethylaminobenzoyl)ethylenediamineYield 62.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In 100 ml of chloroform were dissolved 2.3 g of ethylenediamine and 11.9 ml of triethylamine, followed by adding thereto 50 ml of a chloroform solution containing 15 g of 4-diethylaminobenzoyl chloride with ice-cooling over a period of 30 minutes. Subsequently, the resulting mixture was subjected to reaction at room temperature for 2 hours, after which 100 ml of water was added to the mixture. The chloroform layer was washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The crystals thus obtained were recrystallized from isopropyl alcohol-diisopropyl ether to obtain 9.8 g (62.4% yield) of N,N'-bis(4-diethylaminobenzoyl)ethylenediamine having a melting point of 166° to 167° C.

Workup

  1. additionby adding
  2. temperaturecooling over a period of 30 minutes
  3. customSubsequently, the resulting mixture was subjected to reaction at room temperature for 2 hours
  4. washThe chloroform layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe crystals thus obtained
  8. customwere recrystallized from isopropyl alcohol-diisopropyl ether

Sources & evidence

ORD record
ord-6d92f7b592d34e90af1f7fae5c62c576
Source dataset
uspto-grants-1984_05
Patent number
US04448963

Reaction notes

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