Dichloromethane → 3-Acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline

HRID 1280133Notes

Reaction equation

HRID 1280133 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(Cl)Cl>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:2]([O: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]([O:18][C:16](=[O:17])[CH3:15])[CH2:16][O:17][C:11](=[O:12])[CH3:8])=[O:12])[C:9]=1[I:10])[NH2:6])(=[O:1])[CH3:3]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 184291813-Hydroxymethyl-5-(2,3-dihydroxypropylaminocarbonyl)-2,4,6-triiodoaniline

Product 1

HCID 184291303-Acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

3-Hydroxymethyl-5-(2,3-dihydroxypropylaminocarbonyl)-2,4,6-triiodoaniline (1.89 g, 3.06 mmol) prepared according to Example 3d, was dissolved in a mixture of acetic anhydride (5 ml) and pyridine (5 ml). The mixture was stirred at room temperature for 24 h, CH2Cl2 (100 ml) was added and the solution was washed with water (3×25 ml), with a saturated aqueous solution of NaHCO3, dried (Na2SO4) and evaporated. The product was purified by flash chromatography on silica-gel using a mixture of CH2Cl2 and methanol (98:2) as the eluent.

Workup

  1. washthe solution was washed with water (3×25 ml), with a saturated aqueous solution of NaHCO3
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe product was purified by flash chromatography on silica-gel
  5. additiona mixture of CH2Cl2 and methanol (98:2) as the eluent

Sources & evidence

ORD record
ord-522a74c35ba24d1fb00e8f01597af576
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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