Sodium Iodide → 1-(Ethyloxycarbonyloxy)ethyl 3,5-di(acetylamino)-2,4,6-triiodobenzenecarboxylate

HRID 36788

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

Participants

Conditions

Temperature: 40 °C

Procedure

1-Chloroethyl ethyl carbonate (1.68 g, 11.0 mmol) was added at room temperature to a solution of potassium 3,5-di (acetylamino)-2,4,6-triiodobenzenecarboxylate (6.52 g, 10.0 mmol) and sodium iodide (0.30 g, 2.0 mmol) in dry DMF (100 ml). After stirring at 60° C. for 2 hours and at 40° C. for 65 hours the solvent was removed at reduced pressure. The residue was suspended in chloroform (100 and washed four 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: 2.45 g Purity by HPLC: 98.5% 1H-NMR(DMSO-d6): delta=1.24(CH2CH3); 1.63(CHCH3); 2.02(COCH3); 4.20(CH2CH3); 6.93(CHCH3); 10.03 ppm (NH). FAB/MS: 731 (M+H+)

Workup

customwas removed at reduced pressure
washwashed four 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-6c14c0e043aa46cda61f2d7b2dbbd50d
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05416223

Linked notes

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