Sodium Iodide → HCID 54049765, 화합물

HRID 1084827노트

반응식

HRID 1084827 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 54049765HCID 54049765, 화합물수율 25.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-332925b279994a97a63f9afc684777f3
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05006548

반응 노트

불러오는 중…