Silicon tetrachloride → 4'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl ester

HRID 77777

Reaktionsgleichung

Reaktionsgleichung von HRID 77777
Cl[Si](Cl)(Cl)Cl.[N-:6]=[N+:7]=[N-:8].[Na+].[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[CH:17]=[C:18]([NH:20][C:21](=O)[CH3:22])[CH:19]=1)=[O:13]>C(#N)C>[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[CH:17]=[C:18]([N:20]2[C:21]([CH3:22])=[N:8][N:7]=[N:6]2)[CH:19]=1)=[O:13]

Komponenten

5

Edukt 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 578514405-Acetylamino-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Produkt 1

HCID 578509314'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of tetrachlorosilane (10.07 mmol, 2 mL), NaN3 (30.21 mmol, 1.96 g) and 5-acetylamino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (3.36 mmol, 950.9 mg) in 10 ml of dry acetonitrile was stirred at room temperature for 16 hours. The reaction mixture were poured into ice-cold aqueous Na2CO3 solution and extracted with ethyl acetate (100 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The resulting crude 4′-methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl ester was used for next step directly (880 mg, 85% yield).

Aufarbeitung

  1. additionThe reaction mixture were poured into ice-cold aqueous Na2CO3 solution
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7595477645bf4d2e83e4f7df8e46eb6b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841336B2

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