Sodium Iodide → HCID 22010690, compound

HRID 323158Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:39]=[CH:38][C:20]([C:21]([N:23]([CH3:37])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Cl)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[C:40]1(=[O:50])[NH:44][C:43](=[O:45])[C:42]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:41]12.[K].[I-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:39]=[CH:38][C:20]([C:21]([N:23]([CH3:37])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:44]4[C:43](=[O:45])[C:42]5=[CH:46][CH:47]=[CH:48][CH:49]=[C:41]5[C:40]4=[O:50])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-chloropentyloxy)phenyl]benzamide (800 mg) in N,N-dimethylformamide (15 ml) was added Potassium phthalimide (821 mg) and sodium iodide (cat.) at ambient temperature. The reaction mixture was stirred at 80° C. for 18 hours. The reaction mixture was cooled and extracted with ethyl acetate and washed with water and brine. The organic solution was dried over magnesium sulfate. The solvent was removed by evaporation and subjected to silica gel column chromatography (SiO2; 50 g, 0.5% methanol in chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-phthalimidopentyloxy)phenyl]benzamide (1.1 g).

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate
washwashed with water and brine
dry with materialThe organic solution was dried over magnesium sulfate
customThe solvent was removed by evaporation

Sources & evidence

ORD record: ord-a7efaeac758541bca56e997da9610706
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211242B1

Reaction notes

Loading…