2,4,6-Triiodo-5-(N-methylacetamido)isophthaloyl dichloride → 2,4,6-Triiodo-5-(methylamino)-1,3-benzenedicarbonyl dichloride
Reaction equation
[CH3:1][N:2]([C:6]1[C:7]([I:20])=[C:8]([C:17]([Cl:19])=[O:18])[C:9]([I:16])=[C:10]([C:14]=1[I:15])[C:11]([Cl:13])=[O:12])C(=O)C>C(Cl)(Cl)(Cl)Cl>[CH3:1][NH:2][C:6]1[C:14]([I:15])=[C:10]([C:11]([Cl:13])=[O:12])[C:9]([I:16])=[C:8]([C:7]=1[I:20])[C:17]([Cl:19])=[O:18]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The reaction mixture (now a heterogeneous paste) was poured into a mechanically-stirred slurry of ice water (1:1, 1L), the precipitate filtered and bashed with water (2×100 ml), saturated aqueous sodium bicarbonate (4×200 ml) and finally water to neutral pH (4×300 ml). The product was dried overnight at 40° C. and 0.3 mm Hg over KOH pellet, then redried over P2O5 to yield 5-(N-methyl acetamido)-2,4,6-triiodoisophthaloyl dichloride (XIV) as a slightly off-white, granular solid (60.0 g, 92% yield). TLC (85% CCl4 /15% acetone): Rf (XII):0.79; Rf (XIV):0.59.
Sources & evidence
- ORD record
- ord-912abc6dc78a40079c083d8b3b5fb8d1
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04584401
Reaction notes
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