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

HRID 1184266ノート

反応式

HRID 1184266 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e861037832d647279e94c6b929d52df2
出典データセット
uspto-grants-2014_03
特許番号
US08664380B2

反応ノート

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