Chloroacetic Acid → HCID 22889161, compound

HRID 1654608Notes

Reaction equation

HRID 1654608 reaction equation
[OH:1][P:2]([CH2:5][N:6]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10][N:9]([CH2:15][P:16]([OH:19])([OH:18])=[O:17])[CH2:8][CH2:7]1)([OH:4])=[O:3].Cl[CH2:21][C:22]([OH:24])=[O:23].[OH-].[Na+].Cl>O>[C:22]([CH2:21][N:12]1[CH2:13][CH2:14][N:6]([CH2:5][P:2]([OH:4])([OH:1])=[O:3])[CH2:7][CH2:8][N:9]([CH2:15][P:16]([OH:18])([OH:19])=[O:17])[CH2:10][CH2:11]1)([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 393903HCID 393903, compound

Product 1

HCID 22889161HCID 22889161, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.25 millimoles of N,N'-bis(dihydroxyphosphorylmethyl)-1,4,7-triazacyclononane in water were added 0.3 millimoles of chloroacetic acid, and the pH was adjusted to 9.0 by dropwise, addition of NaOH. The mixture was then heated to 80° C. and held at that temperature overnight. Hydrochloric acid was then added to a pH of 1.5, and the water was evaporated. The solids were then triturated with ether followed by ethanol to remove contaminants, and the remaining solid product was identified by proton NMR as N-carboxymethyl-N',N"-bis(dihydroxyphosphorylmethyl)-1,4,7-triazacyclononane.

Workup

  1. customheld at that temperature overnight
  2. customthe water was evaporated
  3. customThe solids were then triturated with ether
  4. customto remove contaminants

Sources & evidence

ORD record
ord-31c88efe44f344e5b13a4cdb5e6dd0e4
Source dataset
uspto-grants-1995_04
Patent number
US05409689

Reaction notes

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