Sodium Iodide → HCID 54049765, compound

HRID 1084827Notes

Reaction equation

HRID 1084827 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])=[O:9].C(N(CC)CC)C.[C:27](=[O:35])([O:32][CH2:33][CH3:34])[O:28][CH:29](Cl)[CH3:30].[I-].[Na+]>CC(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH:29]([O:28][C:27]([O:32][CH2:33][CH3:34])=[O:35])[CH3:30])=[O:14])=[O:9]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 162095Carbonic acid, 1-chloroethyl ethyl esterHCID 3063368HCID 3063368, compound

Product 1

HCID 54049765HCID 54049765, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-[3-(2-thienyl)acrylamido]benzoic acid (273 mg, 1 mmol) and triethylamine (0.2 ml, 1.4 mmol) in dry acetone (10 ml) was stirred at room temperature for 30 minutes. To the solution, 1-chloroethyl ethyl carbonate (214 mg, 1.4 mmol) and sodium iodide (210 mg, 1.4 mmol) were added under ice cooling, and the mixture was heated under reflux for 19 hours. The reaction mixture was filtered by suction and the solvent was removed from the filtrate. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate, then with saturated aqueous sodium chloride, and dried over magnesium sulfate. After removing the solvent, the residue was purified by silica gel column chromatography (developing solvent:benzene:ether=49:1). The second eluate was collected. After removing the solvent, the resulted oily product was crystallized with isopropyl ether to give the desired compound (98 mg, yield, 25%). m.p., 154°-156° C. (white crystals, recrystallized from methanol/tetrahydrofuran/water).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 19 hours
  3. filtrationThe reaction mixture was filtered by suction
  4. customthe solvent was removed from the filtrate
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with saturated aqueous sodium hydrogen carbonate
  7. dry with materialwith saturated aqueous sodium chloride, and dried over magnesium sulfate
  8. customAfter removing the solvent
  9. customthe residue was purified by silica gel column chromatography (developing solvent:benzene:ether=49:1)
  10. customThe second eluate was collected
  11. customAfter removing the solvent
  12. customthe resulted oily product was crystallized with isopropyl ether

Sources & evidence

ORD record
ord-332925b279994a97a63f9afc684777f3
Source dataset
uspto-grants-1991_04
Patent number
US05006548

Reaction notes

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