Aniline → N3,N6-Bis(carboxymethyl)-N9-phenylcarbamoylmethyl-3,6,9-triazaundecanedioic Acid

HRID 1938139Notes

Reaction equation

HRID 1938139 reaction equation
[C:1]([CH2:4][N:5]([CH2:10][CH2:11][N:12]([CH2:26][C:27]([OH:29])=[O:28])[CH2:13][CH2:14][N:15]([CH2:20][C:21]([O:23]CC)=[O:22])[CH2:16][C:17]([OH:19])=[O:18])[CH2:6][C:7](O)=[O:8])([OH:3])=[O:2].[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CO>[C:17]([CH2:16][N:15]([CH2:14][CH2:13][N:12]([CH2:26][C:27]([OH:29])=[O:28])[CH2:11][CH2:10][N:5]([CH2:6][C:7](=[O:8])[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:4][C:1]([OH:3])=[O:2])[CH2:20][C:21]([OH:23])=[O:22])([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 6115AnilineHCID 54279081Aadobenate Dimeglumine Impurity 3

Product 1

HCID 10205311N3,N6-Bis(carboxymethyl)-N9-phenylcarbamoylmethyl-3,6,9-triazaundecanedioic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 1-liter autoclave, 42.1 g (0.1 mol) of N3,N6 -bis(carboxymethyl)-N9 -ethoxycarbonylmethyl-3,6,9-triazaundecanedioic acid is heated with 93.1 g (1 mol) of aniline for 30 hours to 110° C. After cooling, the content is dissolved in 800 ml of methanol and the solution concentrated to dryness under vacuum. The residue is combined with 800 ml of water and the excess aniline exhaustively extracted with methylene chloride. The aqueous phase is passed, after an initial distillation, over 100 ml of "Amberlite" IR 120. The acidic eluate is concentrated and the residue dried under vacuum at 50° C., thus obtaining 35.1 g (75% of theory) in the form of a white powder with a melting point of 125° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution concentrated to dryness under vacuum
  3. extractionthe excess aniline exhaustively extracted with methylene chloride
  4. distillationafter an initial distillation
  5. concentrationThe acidic eluate is concentrated
  6. customthe residue dried under vacuum at 50° C.
  7. customthus obtaining 35.1 g (75% of theory) in the form of a white powder with a melting point of 125° C.

Sources & evidence

ORD record
ord-52170c58e6354da794918c262f378c33
Source dataset
uspto-grants-1997_12
Patent number
US05693310

Reaction notes

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