Potassium Iodide → 1-(Thenyloxycarbonyloxy)ethyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

HRID 745030Notes

Reaction equation

[C:1](=[O:13])([O:6][CH2:7][C:8]1[S:12][CH:11]=[CH:10][CH:9]=1)[O:2][CH:3](Cl)[CH3:4].[C:14]([NH:17][C:18]1[C:19]([I:34])=[C:20]([N:29]([C:31](=[O:33])[CH3:32])[CH3:30])[C:21]([I:28])=[C:22]([C:25]([O-:27])=[O:26])[C:23]=1[I:24])(=[O:16])[CH3:15].[K+].[I-].[K+]>CN(C=O)C>[C:14]([NH:17][C:18]1[C:19]([I:34])=[C:20]([N:29]([C:31](=[O:33])[CH3:32])[CH3:30])[C:21]([I:28])=[C:22]([C:25]([O:27][CH:3]([O:2][C:1]([O:6][CH2:7][C:8]2[S:12][CH:11]=[CH:10][CH:9]=2)=[O:13])[CH3:4])=[O:26])[C:23]=1[I:24])(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

1-Chloroethyl thenyl carbonate (2.43 g, 11 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (6.66 g, 10 mmol) and potassium iodide (0.17 g, 1 mmol) in dry DMF. After stirring at 50° C. for 5 hours and at room temperature for 4 days the solvent was removed at reduced pressure. The residue was suspended in chloroform (100 ml) and washed three times with a saturated sodium hydrogen carbonate solution and finally twice with water. After drying with magnesium sulfate the solution was evaporated to dryness. Yield: 7.9 g. Purity by HPLC: 88%. 1H-NMR (DMSO-d6): delta=1.64 (CHCH3); 1.65 (N(CH3)COCH3); 2.05 (NCOCH3); 2.95 (NCH3); 5.41 (CH2); 7.00 (CHCH3); 7.05; 7.25; 7.61 (thiophene); 10.11 ppm (NH).

Workup

customwas removed at reduced pressure
washwashed three times with a saturated sodium hydrogen carbonate solution
dry with materialAfter drying with magnesium sulfate the solution
customwas evaporated to dryness

Sources & evidence

ORD record: ord-c40f5d97626542c4b9a02e66d99c2d77
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559266

Reaction notes

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