Potassium Iodide → HCID 15137286, compound

HRID 1741561Notes

Reaction equation

HRID 1741561 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:16][N:15]([CH2:17][C:18]([OH:20])=[O:19])[CH2:14][CH2:13][N:12]([CH2:21][C:22]([OH:24])=[O:23])[CH2:11][C:10]2[N:25]=[C:6]([CH:7]=[CH:8][CH:9]=2)[CH2:5][N:4]1[CH2:26][C:27]([OH:29])=[O:28].[I-].[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:32]([O:1][CH2:2][CH:3]1[CH2:16][N:15]([CH2:17][C:18]([OH:20])=[O:19])[CH2:14][CH2:13][N:12]([CH2:21][C:22]([OH:24])=[O:23])[CH2:11][C:10]2[N:25]=[C:6]([CH:7]=[CH:8][CH:9]=2)[CH2:5][N:4]1[CH2:26][C:27]([OH:29])=[O:28])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 15137284HCID 15137284, compound

Product 1

HCID 15137286HCID 15137286, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g (=24.36 mmol) of 4-hydroxymethyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-3,6,9-triacetic acid (prepared according to Example 7(b) in 150 ml of dimethylformamide is combined with 0.5 g of potassium iodide, 4.17 g of benzyl bromide, and 5 g of sodium carbonate. The mixture is heated for 20 hours to 60° C., concentrated under vacuum, combined with 100 ml of water and 300 ml of ethanol, and the pH is set at 2 by addition of concentrated hydrochloric acid. The mixture is suctioned off from the precipitate, the precipitate is dissolved in 100 ml of water, and the solution is passed over a column with 50 g of "Reillex" (poly-4-vinylpyridine). The column is washed with 50 ml of water and the combined aqueous phases are subjected to freeze-drying, thus obtaining 8 g of the title compound as an amorphous powder.

Workup

  1. temperatureThe mixture is heated for 20 hours to 60° C.
  2. concentrationconcentrated under vacuum
  3. additionthe pH is set at 2 by addition of concentrated hydrochloric acid
  4. dissolutionthe precipitate is dissolved in 100 ml of water
  5. washThe column is washed with 50 ml of water
  6. customto freeze-drying

Sources & evidence

ORD record
ord-5bf7053d5aab43b595c7b3ed2d541ed8
Source dataset
uspto-grants-1994_08
Patent number
US05334371

Reaction notes

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