Toluene → Acetic acid 1-acetoxymethyl-2-[3-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-5-isocyanato-benzoylamino]-ethyl ester

HRID 1038274Notes

Reaction equation

HRID 1038274 reaction equation
[C:1]([O:4][CH2:5][CH:6]([O:35][C:36](=[O:38])[CH3:37])[CH2:7][NH:8][C:9](=[O:34])[C:10]1[C:15]([I:16])=[C:14]([C:17](=[O:30])[NH:18][CH2:19][CH:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:21][O:22][C:23](=[O:25])[CH3:24])[C:13]([I:31])=[C:12]([NH2:32])[C:11]=1[I:33])(=[O:3])[CH3:2].[C:39](Cl)(Cl)=[O:40].C1(C)C=CC=CC=1>O1CCOCC1>[C:23]([O:22][CH2:21][CH:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][NH:18][C:17](=[O:30])[C:14]1[C:13]([I:31])=[C:12]([N:32]=[C:39]=[O:40])[C:11]([I:33])=[C:10]([C:9](=[O:34])[NH:8][CH2:7][CH:6]([O:35][C:36](=[O:38])[CH3:37])[CH2:5][O:4][C:1](=[O:3])[CH3:2])[C:15]=1[I:16])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 98975345-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide Tetraacetate

Product 1

HCID 10463456Acetic acid 1-acetoxymethyl-2-[3-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-5-isocyanato-benzoylamino]-ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of acetic acid 1-acetoxymethyl-2-[3-amino-5-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-benzoylamino]-ethyl ester (15 g, 17 mmol) in 1,4-dioxane (40 mL) was added a solution of 20% phosgene in toluene (100 mL, 11 eq) at ambient temperature. The mixture was then heated to 60° C. for 15 hours. The reaction mixture was cooled to ambient temperature and then concentrated at reduced pressure to give an off white solid. Dioxane (50 mL×2) was added and removed slowly at reduced pressure to give an off-white solid which was placed on a vacuum line to remove any residual solvent. The material was used without further purification

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated at reduced pressure
  3. customto give an off white solid
  4. customremoved slowly at reduced pressure
  5. customto give an off-white solid which
  6. customto remove any residual solvent
  7. customThe material was used without further purification

Sources & evidence

ORD record
ord-a0893cd20310432383d05715b41bfcc1
Source dataset
uspto-grants-2013_10
Patent number
US08551449B2

Reaction notes

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