Sodium Bicarbonate → HCID 54011493, compound

HRID 2379384Notes

Reaction equation

HRID 2379384 reaction equation
C(NC1C(I)=C(C(I)=C(NC(=O)C)C=1I)C(Cl)=O)(=O)C.C(=O)(O)[O-].[Na+].IC1C=CC(C(N)=O)=C(I)C=1I.[OH:38][CH:39]([CH2:61][OH:62])[CH2:40][NH:41][C:42]([C:44]1[C:49](I)=[C:48]([NH:51][C:52](=[O:54])[CH3:53])[C:47](I)=[C:46]([NH:56][C:57](=[O:59])[CH3:58])[C:45]=1I)=[O:43].[F:63][C:64]([F:69])([F:68])C([O-])=O.[Na+]>CN(C)C=O.CN(C)C(=O)C.[Cu]I>[OH:38][CH:39]([CH2:61][OH:62])[CH2:40][NH:41][C:42]([C:44]1[C:49]([C:64]([F:69])([F:68])[F:63])=[C:48]([NH:51][C:52](=[O:54])[CH3:53])[C:47]([C:64]([F:69])([F:68])[F:63])=[C:46]([NH:56][C:57](=[O:59])[CH3:58])[C:45]=1[C:64]([F:69])([F:68])[F:63])=[O:43]

Participants

9

Reactant 5

HCID 516892Sodium BicarbonateHCID 517019Sodium TrifluoroacetateHCID 160896703,5-Diacetamido-2,4,6-triiodobenzoyl chlorideHCID 18429164HCID 18429164, compoundHCID 86139963HCID 86139963, compound

Product 1

HCID 54011493HCID 54011493, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 3,5-bis(acetylamino)-2,4,6-triiodobenzoyl chloride (32 g, 50 mmol), N-(2,3-dihydroxypropyl)-3-aminomethyl-2,2,5,5-tetramethyl-1-pyrrolidinyloxy, free radical (12.3 g, 50 mmol) and sodium bicarbonate (4.2 g, 50 mmol) in 100 mL of dimethyl formamide is stirred for 18 hours at room temperature. The solvent is evaporated under reduced pressure. The residue is purified by C18 chromatography to give the spin labelled triiodobenzenecarboxamide. The chemical reaction is shown below: ##STR24## A mixture of N-((2,2,5,5-tetramethyl-1-pyrrolidinyloxy)methyl, free radical)-N-(2,3-dihydroxypropyl)-3,5-bis(acetylamino)-2,4,6-triiodobenzenecarboxamide (21 g, 25 mmol), sodium trifluoroacetate (61.2 g, 450 mmol) and copper(I) iodide (42.8 g, 225 mmol) in 500 mL of N,N dimethylacetamide is refluxed under argon for six hours. The solvent is evaporated under reduced pressure. The residue is purified by C18 chromatography to give N-((2,2,5,5-tetramethyl-1-pyrrolidinyloxy)methyl, free radical)-N-(2,3-dihydroxypropyl)-3,5-bis(acetylamino)-2,4,6-tris(trifluoromethyl)benzenecarboxamide. The chemical reaction is shown below: ##STR25##

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customThe residue is purified by C18 chromatography
  3. customto give the spin
  4. customThe chemical reaction
  5. temperatureis refluxed under argon for six hours
  6. customThe solvent is evaporated under reduced pressure
  7. customThe residue is purified by C18 chromatography

Sources & evidence

ORD record
ord-9aa98c8984984c579e9493c8ff5a4ce6
Source dataset
uspto-grants-1994_11
Patent number
US05362477

Reaction notes

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