3-Amino-2,4,6-triiodo-5-(methylcarbamoyl)benzoyl chloride → 5-(2,3-Diacetoxypropionylamino)-3-methylcarbamoyl-2,4,6-triiodobenzoyl chloride

HRID 1707904Notes

Reaction equation

HRID 1707904 reaction equation
[NH2:1][C:2]1[C:3]([I:17])=[C:4]([C:13](=[O:16])[NH:14][CH3:15])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:9])=[O:8].C(OCC(NC1C(I)=C(C(=O)NC)C(I)=C(C=1I)C(Cl)=O)=O)(=O)C.[C:42]([O:45][CH:46]([CH2:50][O:51][C:52](=[O:54])[CH3:53])[C:47](Cl)=[O:48])(=[O:44])[CH3:43]>CC(N(C)C)=O>[C:42]([O:45][CH:46]([CH2:50][O:51][C:52](=[O:54])[CH3:53])[C:47]([NH:1][C:2]1[C:3]([I:17])=[C:4]([C:13](=[O:16])[NH:14][CH3:15])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:9])=[O:8])=[O:48])(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 156706213-Amino-2,4,6-triiodo-5-(methylcarbamoyl)benzoyl chloride2×HCID 156706225-Acetoxyacetamido-3-methylcarbamoyl2,4,6-triiodobenzoyl chlorideHCID 189602932,3-Diacetoxypropanoyl chloride

Product 1

HCID 189602905-(2,3-Diacetoxypropionylamino)-3-methylcarbamoyl-2,4,6-triiodobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Compound (11) is prepared from compound (2) in an analogous manner as compound (3) described in Example I, B. Thus, 5-amino-3-methylcarbamoyl-2,4,6-triiodobenzoyl chloride (2) reacted with 2,3-diacetoxypropionyl chloride in DMAc provides 5-(2,3-diacetoxypropionylamino)-3-methylcarbamoyl-2,4,6-triiodobenzoyl chloride (11) in approximately 90% yield.

Sources & evidence

ORD record
ord-a6f2734cee1742e2b612e19d06ac91ed
Source dataset
uspto-grants-1994_10
Patent number
US05356613

Reaction notes

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