Sodium Hydroxide → 1-(2-chlorophenyl)-5-(4-methoxybutyl)-1H-1,2,3-triazole-4-carboxylic acid

HRID 1509601노트

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HRID 1509601 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=O)[CH2:8][C:9]([O:11]C)=[O:10].[N:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[N+:15]=[N-:16].CO.C[O-].[Na+].[OH-].[Na+]>CO>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[C:8]([C:9]([OH:11])=[O:10])[N:16]=[N:15]1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 114124881-Azido-2-chlorobenzeneHCID 23694274Sodium methanolate methanolHCID 58355424Methyl 7-methoxy-3-oxoheptanoate

생성물 1

HCID 583556711-(2-chlorophenyl)-5-(4-methoxybutyl)-1H-1,2,3-triazole-4-carboxylic acid수율 57.8%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

A solution of methyl 7-methoxy-3-oxoheptanoate (2.0 g) in methanol (70 ml) was cooled to 0° C.-5° C., 1-azido-2-chlorobenzene (1.08 g) and 28% sodium methoxide methanol solution (2 g) were added and the mixture was stirred at 60° C. for 3 hr. Then, 1N sodium hydroxide (14 ml) was added, and the mixture was stirred at 60° C. for 1 hr. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue. 1N Hydrochloric acid was added for neutralization and the mixture was extracted with ethyl acetate (50 ml×2). The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (1.26 g) as a powder.

후처리

  1. stirringthe mixture was stirred at 60° C. for 1 hr
  2. customThe solvent was evaporated under reduced pressure and water (20 ml)
  3. additionwas added to the residue
  4. addition1N Hydrochloric acid was added for neutralization
  5. extractionthe mixture was extracted with ethyl acetate (50 ml×2)
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. washa fraction eluted with ethyl acetate
  9. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7ecfdb53a7b442c9a3951b4eae6a7927
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221836B2

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