Sodium Carbonate → 5-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

HRID 84743

Reaktionsgleichung

Reaktionsgleichung von HRID 84743
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[CH:12]=[C:13]([C:15](=O)[NH:16][CH2:17][CH3:18])[CH:14]=1)=[O:8].[Si](Cl)(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[CH:12]=[C:13]([C:15]2[N:16]([CH2:17][CH3:18])[N:3]=[N:2][N:1]=2)[CH:14]=1)=[O:8]

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 578516275-Ethylcarbamoyl-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Produkt 1

HCID 578516285-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Sodium azide (145.8 mg, 16.2 mmol) was added into a solution of 5-ethylcarbamoyl-4′-methyl-biphenyl-3-carboxylic acid methyl ester (210 mg, 0.7 mmol) and SiCl4 (0.62 mL, 5.4 mmol) in dry acetonitrile (14 mL). After the reaction was stirred at room temperature for 24 hours, the reaction mixture was poured into cold saturated aqueous Na2CO3 solution. This mixture was extracted with ethyl acetate and dried with anhydrous Na2SO4. Solvent was removed under reduced pressure to afford 200 mgs of 5-(1-ethyl-1H-tetrazol-5-yl)-4′-methyl-biphenyl-3-carboxylic acid methyl ester (yield 89%). MS (M+H)=323.

Aufarbeitung

  1. extractionThis mixture was extracted with ethyl acetate
  2. dry with materialdried with anhydrous Na2SO4
  3. customSolvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-50f6b3cbd72d4b62a2373eb5eed565d3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846945B2

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