Citric Acid → HCID 70360585, compound

HRID 330417Notes

Reaction equation

HRID 330417 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[C:9](N1C=CN=C1)(N1C=CN=C1)=[O:10].[CH2:21]([N:23]([CH2:36][CH3:37])[CH2:24][CH2:25][NH:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:22].[C:38]([OH:50])(=[O:49])[CH2:39][C:40]([CH2:45][C:46]([OH:48])=[O:47])([C:42]([OH:44])=[O:43])[OH:41]>O1CCCC1.CO.C(OCC)C>[C:38]([OH:50])(=[O:49])[CH2:39][C:40]([CH2:45][C:46]([OH:48])=[O:47])([C:42]([OH:44])=[O:43])[OH:41].[CH2:36]([N:23]([CH2:21][CH3:22])[CH2:24][CH2:25][N:26]([CH2:27][CH2:28][O:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:9]([NH:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[O:10])[CH3:37]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 14855237HCID 14855237, compound

Product 1

HCID 70360585HCID 70360585, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2.72 g (0.0235 mole) of N,N-diethylethylenediamine and 4.37 g (0.027 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.11 g (0.0216 mole) of N,N-diethyl-N'-(2-phenoxyethyl)-1,2-ethanediamine in 50 ml of tetrahydrofuran was added, and the solution was refluxed for 20 hr. The solvent was removed in vacuo and the residue was dissolved in a mixture of 250 ml of diethyl ether and 250 ml of methylene chloride. The solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. A solution of the oil in methanol was treated with a two-fold excess of citric acid, diethyl ether was added, and 12.22 g (74.2%) of the title compound crystallized as a white crystalline solid, m.p. 80°-85° C.

Workup

  1. temperaturethe solution was refluxed for 20 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in a mixture of 250 ml of diethyl ether and 250 ml of methylene chloride
  4. extractionThe solution was extracted with several portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give an oil
  8. additionwas added
  9. custom12.22 g (74.2%) of the title compound crystallized as a white crystalline solid, m.p. 80°-85° C.

Sources & evidence

ORD record
ord-a56de747efbd4d399780be43d6492520
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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