Hydrochloric Acid → 1-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethanone

HRID 2422727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422727
C[Mg]Br.[CH2:4](N(CC)CC)C.[CH3:11][C:12]1[CH:13]=[C:14]([N:18]2[N:22]=[N:21][C:20]([C:23]([O:25]CC)=O)=[N:19]2)[CH:15]=[CH:16][CH:17]=1.Cl>C1(C)C=CC=CC=1.O>[CH3:11][C:12]1[CH:13]=[C:14]([N:18]2[N:22]=[N:21][C:20]([C:23](=[O:25])[CH3:4])=[N:19]2)[CH:15]=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 25264098ethyl 2-m-tolyl-2H-tetrazole-5-carboxylateHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 252640991-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethanoneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Methylmagnesium bromide (1070 mL, 1.50 mol, 1.4 M in tetrahydrofuran/toluene) in triethylamine (520 mL, 3.74 mol) was added via an addition funnel to a stirred solution of ethyl 2-(3-methylphenyl)-2H-tetrazole-5-carboxylate in dry toluene (1000 mL) at −10° C. for 5 hours. The mixture was continued to stir at −10° C. overnight. A cooled (+3° C.) solution of hydrochloric acid (37%, 500 mL) and water (500 mL) was added over 2 hours 20 minutes. The layers were separated and the organic layer was washed with water (500 mL) and brine (2×250 mL). The aqueous layer was extracted with toluene (3×500 mL) and the toluene was washed with brine (2×250 mL). The combined organic extracts were concentrated and purified on silica using dichloromethane as eluent. The concentrated product residue was triturated with petroleum ether, filtrated and dried under reduced pressure at room temperature to give the title product (90.86 g, 60%).

Aufarbeitung

  1. additionwas added over 2 hours 20 minutes
  2. customThe layers were separated
  3. washthe organic layer was washed with water (500 mL) and brine (2×250 mL)
  4. extractionThe aqueous layer was extracted with toluene (3×500 mL)
  5. washthe toluene was washed with brine (2×250 mL)
  6. concentrationThe combined organic extracts were concentrated
  7. custompurified on silica
  8. customThe concentrated product residue was triturated with petroleum ether
  9. filtrationfiltrated
  10. customdried under reduced pressure at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-7157c50a30df46abb3e7178b3cb58412
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960422B2

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