Hydrochloric Acid → HCID 18429363, compound

HRID 1280171Notes

Reaction equation

HRID 1280171 reaction equation
[C:1]([O:4][CH:5]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[C:6]([NH:8][C:9]1[C:10]([I:31])=[C:11]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C:12]([I:25])=[C:13]([C:23]=1[I:24])[C:14]([NH:16][CH2:17][CH2:18][O:19][C:20](=[O:22])[CH3:21])=[O:15])=[O:7])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:43](Br)[CH:44]=[CH2:45].Cl>CS(C)=O>[CH2:45]([N:8]([C:6](=[O:7])[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:32][O:33][C:34](=[O:36])[CH3:35])[C:9]1[C:10]([I:31])=[C:11]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C:12]([I:25])=[C:13]([C:23]=1[I:24])[C:14]([NH:16][CH2:17][CH2:18][O:19][C:20](=[O:22])[CH3:21])=[O:15])[CH:44]=[CH2:43]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 18429260HCID 18429260, compound

Product 1

HCID 18429363HCID 18429363, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-(2,3-Diacetoxypropionylamino)-3-acetoxymethyl-N-(2-acetoxyethyl)-2,4,6-triiodobenzamide (8.65 g, 10.3 mmol) was dissolved in dimethyl sulfoxide (10 ml) at room temperature. Cesium carbonate (3.88 g, 11.8 mmol) was added and after stirring at room temperature for 15 min, the mixture was cooled in an ice bath. Allyl bromide (2.10 g, 17.3 mmol) was added dropwise and the mixture was then stirred for 17 h at room temperature. The reaction mixture was transferred onto aqueous hydrochloric acid (0.1 M, 300 ml). The formed precepitate was filtered off, redissolved in methylene chloride (150 ml) and washed with water (5×100 ml). The organic phase was dried (Na2SO4), and the solvent evaporated. Yield: 8.73 g (96%).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. stirringthe mixture was then stirred for 17 h at room temperature
  3. filtrationThe formed precepitate was filtered off
  4. dissolutionredissolved in methylene chloride (150 ml)
  5. washwashed with water (5×100 ml)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-f9d6e443b26c40e4b66dc33e933e23fc
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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