Diethyl (2-bromoethyl)phosphonate → Diethyl 2-(3,5-Bis-acetylamino-2,4,6-triiodobenzovloxy)ethylphosphonate

HRID 2229993Notes

Reaction equation

HRID 2229993 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[C:10]([I:11])=[C:9]([NH:12][C:13]([CH3:15])=[O:14])[C:8]([I:16])=[C:7]([C:17]([O-:19])=[O:18])[C:6]=1[I:20])=[O:3].[Na+].Br[CH2:23][CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]>CN(C)C=O>[C:13]([NH:12][C:9]1[C:8]([I:16])=[C:7]([C:6]([I:20])=[C:5]([NH:4][C:2](=[O:3])[CH3:1])[C:10]=1[I:11])[C:17]([O:19][CH2:23][CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[O:18])(=[O:14])[CH3:15]

Participants

4

Reactant 2

HCID 79218Diethyl (2-bromoethyl)phosphonateHCID 23672589Sodium Amidotrizoate

Product 1

HCID 18464015Diethyl 2-(3,5-Bis-acetylamino-2,4,6-triiodobenzovloxy)ethylphosphonateYield 41.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of sodium diatrizoate (7.1 g, 11.2 mmol) in dry dimethylformamide (50 ml) at room temperature under a blanket of argon was added a solution of diethyl 2-bromoethylphosphonate (3.02 g, 12.3 mmol, 1.1 eq.) in dimethylformamide (10 ml). After stirring for 12 hours, the solvent was evaporated under vacuum to give a white solid that was washed with 300 ml of saturated aqueous NaHCO3, and then extracted with a 2:1 mixture of chloroform-ethanol (3×200 ml). The organic extract was dried (MgSO4), filtered, and evaporated under vacuum to give 3.61 g (41%) of product as a white solid. Recrystallization from acetonitrile gave analytically pure material; mp 249-251° C.; MH+ (779). The 1H-NMR (300 MHz) spectrum was consistent with the desired material.

Workup

  1. customthe solvent was evaporated under vacuum
  2. customto give a white solid
  3. washthat was washed with 300 ml of saturated aqueous NaHCO3
  4. extractionextracted with a 2:1 mixture of chloroform-ethanol (3×200 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-0152b8cd12b64dd389c46c9225f7b83f
Source dataset
uspto-grants-2002_07
Patent number
US06423296B1

Reaction notes

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