Water → 2-(2-Thienylcarbonyl)benzoic acid

HRID 1769116ノート

反応式

HRID 1769116 の反応式
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[Cl-].[Al+3].[Cl-].[Cl-].[S:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.O>[N+](C1C=CC=CC=1)([O-])=O>[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])=[O:5]

参加物

6

反応物 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 8030ThiopheneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 2826542-(2-Thienylcarbonyl)benzoic acid収率 27%

試薬・触媒・溶媒 1

HCID 7416Nitrobenzene溶媒

実験手順

A solution of 74.1 g (0.5 mole) of phthalic anhydride in 300 mL of nitrobenzene was treated with 147 g (1.1 mole) of aluminum chloride. The solution was stirred for two hours and 42.1 g (0.5 mole) of thiophene was added dropwise over 80 minutes at 40°-45°. The reaction was stirred at 50°-55° for two hours and then let sit at room temperature overnight. The reaction was poured into 2.8 L of cold water, stirred, separated, and the nitrobenzene was removed from the nitrobenzene layer by steam distillation. The residue was recrystallized from toluene to provide 31.1 g (27%) of 2-thienoylbenzoic acid, mp 141-143. The thienoylbenzoic acid was treated with methylhydrazine as described in Example 185 to provide 24.4 g (75%) of the phthalazinone product, mp 143-144, after recrystallization from ethyl acetate.

後処理

  1. stirringThe reaction was stirred at 50°-55° for two hours
  2. waitlet sit at room temperature overnight
  3. stirringstirred
  4. customseparated
  5. customthe nitrobenzene was removed from the nitrobenzene layer by steam distillation
  6. customThe residue was recrystallized from toluene

出典と根拠

ORDレコード
ord-ec04c2fda50c48c48a03bb000da40d45
出典データセット
uspto-grants-1995_01
特許番号
US05380721

反応ノート

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