Thionyl Chloride → HCID 54139106, compound

HRID 233425Notes

Reaction equation

HRID 233425 reaction equation
[NH2:1][C:2]1[C:3]([I:42])=[C:4]([C:8]([I:41])=[C:9]([C:12](=[O:40])[NH:13][CH2:14][CH:15]([O:36][C:37](=[O:39])[CH3:38])[CH:16]([O:32][C:33](=[O:35])[CH3:34])[CH:17]([O:28][C:29](=[O:31])[CH3:30])[CH:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:19][O:20][C:21](=[O:23])[CH3:22])[C:10]=1[I:11])[C:5](O)=[O:6].S(Cl)([Cl:45])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[NH2:1][C:2]1[C:3]([I:42])=[C:4]([C:8]([I:41])=[C:9]([C:12](=[O:40])[NH:13][CH2:14][CH:15]([O:36][C:37](=[O:39])[CH3:38])[CH:16]([O:32][C:33](=[O:35])[CH3:34])[CH:17]([O:28][C:29](=[O:31])[CH3:30])[CH:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:19][O:20][C:21](=[O:23])[CH3:22])[C:10]=1[I:11])[C:5]([Cl:45])=[O:6]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 23355826HCID 23355826, compound

Product 1

HCID 54139106HCID 54139106, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

15.5 g (16.4 mmol) of 3-amino-5-(2,3,4,5,6-pentaacetoxyhexylcarbamoyl)-2,4,6-triiodobenzoic acid [Example 18a)] is suspended in 80 ml of ethyl acetate and refluxed with 1.9 ml (24.6 mmol) of thionyl chloride for 5 hours. The reaction mixture is added to 30 g of sodium bicarbonate in 300 ml of water and stirred vigorously for 1.5 hours. Then, the phases are separated and the organic phase is dried on sodium sulfate, filtered, and the solution is concentrated by evaporation. The oily reaction product is foamed up in a high vacuum.

Workup

  1. customThen, the phases are separated
  2. customthe organic phase is dried on sodium sulfate
  3. filtrationfiltered
  4. concentrationthe solution is concentrated by evaporation

Sources & evidence

ORD record
ord-5d064e56fc0044dea1e740ca310a82ef
Source dataset
uspto-grants-1997_01
Patent number
US05593660

Reaction notes

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