Water → 2-(2-Thienylcarbonyl)benzoic acid

HRID 54971노트

반응식

HRID 54971 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 2826542-(2-Thienylcarbonyl)benzoic acid수율 27%

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-badfe0d6a3f14dbbb8f39bceae2caad5
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624922

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