Phosgene → HCID 18429324, compound

HRID 1280134

Reaction equation

HRID 1280134 reaction equation
[C:1]([O:4][CH:5]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH2:6][NH:7][C:8]([C:10]1[C:11]([I:33])=[C:12]([C:14]([I:32])=[C:15]([C:18]([NH:20][CH2:21][CH:22]([O:28][C:29](=[O:31])[CH3:30])[CH2:23][O:24][C:25](=[O:27])[CH3:26])=[O:19])[C:16]=1[I:17])[NH2:13])=[O:9])(=[O:3])[CH3:2].[C:39](Cl)(Cl)=[O:40].[C:43]([O:46][CH2:47][C:48]1[C:49]([I:71])=[C:50]([C:52]([I:70])=[C:53]([C:56]([NH:58][CH2:59][CH:60]([O:66][C:67](=[O:69])[CH3:68])[CH2:61][O:62][C:63](=[O:65])[CH3:64])=[O:57])[C:54]=1[I:55])[NH2:51])(=[O:45])[CH3:44]>O1CCOCC1.C1(C)C=CC=CC=1.[Hg](OC(C(F)(F)F)=O)OC(C(F)(F)F)=O>[C:43]([O:46][CH2:47][C:48]1[C:49]([I:71])=[C:50]([NH:51][C:39]([NH:13][C:12]2[C:11]([I:33])=[C:10]([C:8]([NH:7][CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:34][O:35][C:36](=[O:38])[CH3:37])=[O:9])[C:16]([I:17])=[C:15]([C:18]([NH:20][CH2:21][CH:22]([O:28][C:29](=[O:31])[CH3:30])[CH2:23][O:24][C:25](=[O:27])[CH3:26])=[O:19])[C:14]=2[I:32])=[O:40])[C:52]([I:70])=[C:53]([C:56]([NH:58][CH2:59][CH:60]([O:66][C:67](=[O:69])[CH3:68])[CH2:61][O:62][C:63](=[O:65])[CH3:64])=[O:57])[C:54]=1[I:55])(=[O:45])[CH3:44]

Participants

7

Reactant 3

HCID 6371PhosgeneHCID 98975345-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide TetraacetateHCID 18429130HCID 18429130, compound

Product 1

HCID 18429324HCID 18429324, compound

Reagents, catalysts & solvents 3

HCID 16685285Hg(TFA)2CatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

3,5-Bis(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline (260 mg, 0.30 mmol) was dissolved in dioxane (1.0 ml) and a solution of phosgene in toluene (1.93 M, 1.8 ml) was added. The flask was tightly sealed and then heated to 60° C. for 17 h. After cooling to room temperature, the solvent was distilled off at reduced pressure. Dioxane (3 ml) was added and distilled off again. This procedure was repeated twice. Dioxane (1 ml) was added followed by 3-acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline (0.245 g, 0.31 mmol), prepared according to Example 16a, and Hg(OCOCF3)2 (20 mg). The mixture was stirred for 16 h at room temperature, the solvent was evaporated and the residue was purified by preparative HPLC. Yield: 0.192 g (39%).

Workup

  1. customThe flask was tightly sealed
  2. temperatureAfter cooling to room temperature
  3. distillationthe solvent was distilled off at reduced pressure
  4. additionDioxane (3 ml) was added
  5. distillationdistilled off again
  6. additionDioxane (1 ml) was added
  7. customprepared
  8. customthe solvent was evaporated
  9. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c521745d17b4445a83de0f5063969d20
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Linked notes

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