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Water → 1-(p-Chlorobenzenesulfonyloxy)-1,2,3-benzotriazole

HRID 1733708
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HRID 1733708 반응식
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.O>C1C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:1][N:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N:4]=[N:3]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole

생성물 1

HCID 203000021-(p-Chlorobenzenesulfonyloxy)-1,2,3-benzotriazole수율 87.3%

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

In benzene (40 ml) are dissolved 1-hydroxy-1,2,3-benzotriazole (10.6 g) and triethylamine (11.1 ml). To the solution is added dropwise a solution of p-chlorobenzenesulfonyl chloride (16.6 g) in benzene (8 ml) with stirring under ice-cooling during about 20 minutes, and the mixture is stirred at 15° C. for 4 hours. To the reaction mixture is added water and the benzene layer is separated. The aqueous layer is extracted twice with ethyl acetate (100 ml). The extract is combined with the above benzene layer, washed with a small amount of an aqueous sodium hydrogen carbonate and water in order and dried over anhydrous sodium sulfate. After drying, the solvent is distilled off under a reduced pressure. The resulting crystals are cracked in petroleum ether and separated by filtration and dried to give faint yellow crystals of 1-(p-chlorobenzensulfonyloxy)-1,2,3-benzotriazole (21.2 g), melting point: 94°-95° C. Ultraviolet spectrum (methanol): λmax 224 mμ, E=365.

후처리

  1. temperaturecooling during about 20 minutes
  2. stirringthe mixture is stirred at 15° C. for 4 hours
  3. customthe benzene layer is separated
  4. extractionThe aqueous layer is extracted twice with ethyl acetate (100 ml)
  5. washwashed with a small amount of an aqueous sodium hydrogen carbonate and water in order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter drying
  8. distillationthe solvent is distilled off under a reduced pressure
  9. customseparated by filtration
  10. customdried

출처 및 근거

ORD 기록
ord-80330615c3f24330af5df6c798bb36c1
출처 데이터셋
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04242507

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