Triethylamine → HCID 54376430、化合物

HRID 1084826ノート

反応式

HRID 1084826 の反応式
[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.Br[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:30](=[O:31])[O:29]1>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:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:30](=[O:31])[O:29]1)=[O:14])=[O:9]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 3063368HCID 3063368、化合物

生成物 1

HCID 54376430HCID 54376430、化合物収率 39.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

A mixture of 2-[3-(2-thienyl)acrylamido]benzoic acid (273 mg, 1 mmol) and triethylamine (0.14 ml, 1 mmol) in dry acetone (10 ml) was stirred at room temperature for 30 minutes. A solution of 3-bromophtalide (213 mg, 1 mmol) in acetone (2 ml) was added under ice cooling, and the mixture was stirred at room temperature for 23 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. The solvent was removed and the residue was purified by silica gel column chromatography (developing solvent: benzene:ether=49:1). The pale yellow second eluate was collected. After removing the solvent, the resulting oily product was crystallized with isopropyl ether to give the desired compound (159 mg, yield, 39%). m.p., 194°-195° C. (white crystals, recrystallized from benzene-n-hexane)

後処理

  1. stirringthe mixture was stirred at room temperature for 23 hours
  2. filtrationThe reaction mixture was filtered by suction
  3. customthe solvent was removed from the filtrate
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialwith saturated aqueous sodium chloride, and dried over magnesium sulfate
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel column chromatography (developing solvent: benzene:ether=49:1)
  9. customThe pale yellow second eluate was collected
  10. customAfter removing the solvent
  11. customthe resulting oily product was crystallized with isopropyl ether

出典と根拠

ORDレコード
ord-c178c6e047f24a64943c5a7b641a3ed8
出典データセット
uspto-grants-1991_04
特許番号
US05006548

反応ノート

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