Water → Hexahydro-1H-1,4,7-triazonine-1,4(5H)-diacetic acid

HRID 742531Notes

Reaction equation

HRID 742531 reaction equation
[C:1]([CH2:4][N:5]1[CH2:13][CH2:12][N:11](S(C)(=O)=O)[CH2:10][CH2:9][N:8]([CH2:18][C:19]([OH:21])=[O:20])[CH2:7][CH2:6]1)([OH:3])=[O:2].O>S(=O)(=O)(O)O>[C:1]([CH2:4][N:5]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9][N:8]([CH2:18][C:19]([OH:21])=[O:20])[CH2:7][CH2:6]1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 19426279HCID 19426279, compound

Product 1

HCID 393901Hexahydro-1H-1,4,7-triazonine-1,4(5H)-diacetic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 1,4-bis-(carboxymethyl)-7-methanesulfonyl-1,4,7-triazacyclononane (15.0 g, 0.05 mol) in 15 mL of concentrated sulfuric acid is stirred at 25 C. for 24 hours. The reaction mixture is cooled in an ice bath and 50 mL of water is slowly added. Then the pH of the solution is adjusted to 7 and the solvent is evaporated under reduced pressure. The residue is triturated with methanol several times and the combined methanol solutions are evaporated to give 1,4-bis-(carboxymethyl)-1,4,7-triazacyclononane.

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. customthe solvent is evaporated under reduced pressure
  3. customThe residue is triturated with methanol several times
  4. customthe combined methanol solutions are evaporated

Sources & evidence

ORD record
ord-3eb2ee4a158d41508164716c0d80e90b
Source dataset
uspto-grants-1996_09
Patent number
US05554749

Reaction notes

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