Acetic Acid → N,N'-Bis(salicylidene)ethylenediamine

HRID 2304351Notes

Reaction equation

HRID 2304351 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[C:5]([OH:8])(=O)[CH3:6].[CH:9](=O)[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[OH:12]>C1(C)C=CC=CC=1>[CH:9](=[N:3][CH2:2][CH2:1][N:4]=[CH:13][C:11]1[C:5](=[CH:6][CH:15]=[CH:16][CH:10]=1)[OH:8])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[OH:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 6998Salicylaldehyde

Product 1

HCID 26518N,N'-Bis(salicylidene)ethylenediamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Ethylenediamine (5.71 g, 0.095 mmol) was dissolved into toluene (60 ml). To it, a catalytic amount of acetic acid was added. Then, salicylaldehyde (23.20 g, 0.190 mmol) dissolved into toluene (60 ml) was dropwise added into the above solution. The resulting solution was then stirred at room temperature overnight. A yellowish crystalline product was precipitated. It was filtered, washed with ethanol, and dried. The yield was 23.7 g (93%). 1H NMR (300 MHz, CDCl3): δ=3.84 ppm (s, 4H), 6.85 ppm (t, 2H), 6.92 ppm (d, 2H), 7.17 ppm (m. 2H), 7.19 ppm (m, 2H), 8.28 ppm (s, 2H), 12.77 (s, broad, 2×OH); ESI MS: calcd. for C16H16N2O2, 268.3, found 269.2 (M+1); UV/Vis (λmax, nm, in methanol): 212, 255, 316, 400; IR (cm−1, nujol mull): 1610 (m, —C═N—).

Workup

  1. additionwas dropwise added into the above solution
  2. customA yellowish crystalline product was precipitated
  3. filtrationIt was filtered
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-0673b78ffedf47bf996ce7da62e0ba38
Source dataset
uspto-grants-2002_08
Patent number
US06436171B1

Reaction notes

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