Sodium Iodide → HCID 18924362, compound

HRID 1288638Notes

Reaction equation

HRID 1288638 reaction equation
[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2].Br[CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:26]([N:14]1[CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6][N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:16][CH2:15]1)[CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 1235321-Bromo-3,6-dioxaheptane

Product 1

HCID 18924362HCID 18924362, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g (8.66 mmol) of 1,4,7-tris-(carboxymethyl)-1,4,7, 10-tetraazacyclododecane is stirred in 50 ml of dimethylformamide for 10 hours with 1.83 g (10 mmol) of 1-bromo-3,6-dioxa-heptane, 100 mg of sodium iodide and 4 g of potassium carbonate at 90° C. It is concentrated by evaporation in a vacuum and the residue is spread between 100 ml of water and 50 ml of diethyl ether. The aqueous phase is adjusted to pH 2 with 5 N hydrochloric acid and evaporated to dryness. The residue is refluxed with 200 ml of methanol, the undissolved material is filtered out, evaporated to dryness in a vacuum, the residue is dissolved in 50 ml of water, adjusted to pH 2 with 5 N hydrochloric acid and the solution is put on a column with 200 ml of cation exchanger IRC 50. It is eluted first with 0.5 l of water, which is discarded. Then, it is eluted with 0.5 l of 0.5 N ammonia solution. It is evaporated almost to dryness in a vacuum, mixed with 100 ml of water and enough cation exchanger IRC 50 is added with stirring to reach pH 3.5. The solution is then filtered and freeze-dried. 2.95 g of the title compound with a water content of 3.5% is obtained.

Workup

  1. concentrationIt is concentrated by evaporation in a vacuum
  2. customevaporated to dryness
  3. temperatureThe residue is refluxed with 200 ml of methanol
  4. filtrationthe undissolved material is filtered out
  5. customevaporated to dryness in a vacuum
  6. dissolutionthe residue is dissolved in 50 ml of water
  7. washIt is eluted first with 0.5 l of water, which
  8. washThen, it is eluted with 0.5 l of 0.5 N ammonia solution
  9. customIt is evaporated almost to dryness in a vacuum
  10. additionmixed with 100 ml of water and enough cation exchanger IRC 50
  11. additionis added
  12. filtrationThe solution is then filtered
  13. customfreeze-dried

Sources & evidence

ORD record
ord-90253e2cfdb644428d10ee80793bbb7e
Source dataset
uspto-grants-1998_05
Patent number
US05747000

Reaction notes

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