Sodium Iodide → HCID 22319709, compound

HRID 497575Notes

Reaction equation

HRID 497575 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[C:25]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[CH:24][CH:23]=[CH:22][C:8]=2[C:9]=1[C:10](=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19]Br)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[CH2:32]([NH:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH3:35].[I-].[Na+].[C:43](=[O:46])([O-:45])[O-].[K+].[K+]>C(#N)C>[C:26]([OH:28])(=[O:27])[C:43]([OH:45])=[O:46].[CH2:1]([C:5]1[O:6][C:7]2[C:25]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[CH:24][CH:23]=[CH:22][C:8]=2[C:9]=1[C:10](=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][N:36]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8148DibutylamineHCID 11430Potassium CarbonateHCID 22319704HCID 22319704, compound

Product 1

HCID 22319709HCID 22319709, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.5 g (0.0095 mol) of isopropyl 2-butyl-3-[4-(3-bromopropyl)benzoyl]-1-benzofuran-7-carboxylate are dissolved in 80 ml of acetonitrile. 3.68 g (0.0285 mol) of dibutylamine are then added, followed by 1.42 g (0.0095 mol) of sodium iodide and 3.94 g (0.0285 mol) of potassium carbonate. The mixture is brought to reflux for 15 hours and is then evaporated. Extraction is carried out with diethyl ether and the extract is washed with water and a sodium chloride solution. Purification is subsequently carried out by chromatography on silica (eluent: 100/3/0.2 dichloromethane/methanol/aqueous ammonia), which gives 2.91 g of the desired compound in the free base form (yield: 57%).

Workup

  1. temperatureto reflux for 15 hours
  2. customis then evaporated
  3. extractionExtraction
  4. washthe extract is washed with water
  5. customPurification

Sources & evidence

ORD record
ord-55434eb01a9e4d8cbdbd169abd08f9e9
Source dataset
uspto-grants-2005_09
Patent number
US06949583B2

Reaction notes

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