Sodium Iodide → HCID 19422762, compound

HRID 1491520Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

1-Chloroethyl ethyl carbonate (1.67 g, 11.0 mmol) was added dropwise at room temperature to a solution of potassium 5-(N-acetylamino) -3-(N-methylaminocarbonyl)-2,4,6-triiodobenzenecarboxylate (6.52 g, 10.0 retool) and sodium iodide (150 rag, 1.0 retool) in dry DMF (50 ml). After stirring at 50° C. for 24 hours the solvent was removed at reduced pressure. The residue was dissolved in chloroform and washed four times with a saturated sodium hydrogen carbonate solution and twice with water. After drying with magnesium sulfate and filtration, the solvent was removed at reduced pressure to give the title compound. Yield: (2.2 g, 38 %). Purity by HPLC: 98%. 1H-NMR (DMSO (DMSO-6 ): delta=1.24 (t, J=7 Hz, CH3); 1.63 (d, J=6 Hz, CH3); 2.03 (s, CH3CO); 2.75 (d, J=3 Hz, NCH3); 4.21 (q, J=7 Hz, CH2): 6.93 (q, J=6 Hz, CH); 8.4-8.7 (m, NHMe); 10.03 ppm (s, NHAc).

Workup

customwas removed at reduced pressure
dissolutionThe residue was dissolved in chloroform
washwashed four times with a saturated sodium hydrogen carbonate solution
dry with materialAfter drying with magnesium sulfate and filtration
customthe solvent was removed at reduced pressure

Sources & evidence

ORD record: ord-321846efb8774f5786c9b484c58c957b
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05370861

Reaction notes

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