Hydrochloric Acid → 1,4,7-Triazacyclononane-N,N',N''-triacetic acid

HRID 1595935Notes

Reaction equation

HRID 1595935 reaction equation
[NH:1]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:11][C:12]([O-:14])=[O:13].[Na+].Cl>>[C:12]([CH2:11][N:1]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]([OH:14])=[O:13])[CH2:6][CH2:5][N:4]([CH2:11][C:12]([OH:14])=[O:13])[CH2:3][CH2:2]1)([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1883181,4,7-TriazacyclononaneHCID 23665759Sodium chloroacetate

Product 1

HCID 1243261,4,7-Triazacyclononane-N,N',N''-triacetic acid

Conditions

Temperature
80 °C

Procedure

To an aqueous solution of TACN (0.16 mols in 58 mL water) is added an aqueous solution of sodium chloroacetate (0.71 mols sodium chloroacetate in 68 mL of water). This solution is stirred at 80° C. overnight while maintaining the pH at 9-10. After cooling to ambient temperature the pH of the solution is adjusted to 2.5 with aqueous HCl. The resulting precipitate is collected by filtration, washed with acetone, and dried in vacuo to afford the mono-hydrochloride salt of 1,4,7-tricarboxymethyl-1,4,7-triazacyclononane.

Workup

  1. temperaturewhile maintaining the pH at 9-10
  2. temperatureAfter cooling to ambient temperature the pH of the solution
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with acetone
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d85d095bc3264069811c66366a03ceed
Source dataset
uspto-grants-2001_09
Patent number
US06288224B1

Reaction notes

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