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

HRID 1184266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184266
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 583556711-(2-chlorophenyl)-5-(4-methoxybutyl)-1H-1,2,3-triazole-4-carboxylic acidAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e861037832d647279e94c6b929d52df2
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664380B2

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