Sulfuric Acid → N-acetyl-3-acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline

HRID 383003Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:4]([I:20])=[C:5]([C:7]([I:19])=[C:8]([C:11]([NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])=[O:12])[C:9]=1[I:10])[NH2:6].C(O[C:25](=[O:27])[CH3:26])(=O)C.S(=O)(=O)(O)O.C(Cl)Cl>C(O)(=O)C.O>[C:2]([NH:6][C:5]1[C:7]([I:19])=[C:8]([C:11]([NH:13][CH2:14][CH:15]([O:18][C:16](=[O:17])[CH3:15])[CH2:16][O:17][C:11](=[O:12])[CH3:8])=[O:12])[C:9]([I:10])=[C:3]([CH2:2][O:1][C:25](=[O:27])[CH3:26])[C:4]=1[I:20])(=[O:1])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

3-Hydroxymethyl-5-(2,3-dihydroxypropylaminocarbonyl)-2,4,6-triiodoaniline (3.3 g, 5.3 mmol) was suspended in glacial acetic acid (12 ml) containing acetic anhydride (48 ml) and concentrated sulfuric acid (0.08 ml). The mixture was stirred at 60° C. for 3 h, allowed to cool to room temperature, and CH2Cl2 (100 ml) and water (100 ml) were added. The organic phase was washed with water (3×50 ml) and a saturated aqueous solution of NaHCO3 (2×50 ml). After drying (MgSO4) and evaporation, the residue was dissolved in a mixture of CH2Cl2 and methanol (9:1) and filtered through a short silica pad and evaporated. Yield: 3.0 g (71%).

Workup

temperatureto cool to room temperature
washThe organic phase was washed with water (3×50 ml)
customAfter drying
custom(MgSO4) and evaporation
dissolutionthe residue was dissolved in a mixture of CH2Cl2 and methanol (9:1)
filtrationfiltered through a short silica pad
customevaporated

Sources & evidence

ORD record: ord-29e9978dcaf94e81b0048e5288bbdc14
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310243B1

Reaction notes

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