Triethylamine → [1,1'-Biphenyl]-3-carbonyl azide

HRID 62071

Reaktionsgleichung

Reaktionsgleichung von HRID 62071
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[C:25]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][CH:28]=[C:27]([C:31](O)=[O:32])[CH:26]=1>C(O)(C)C>[C:25]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([N:15]=[N+:16]=[N-:17])=[O:32])[CH:26]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Produkt 1

HCID 118675061[1,1'-Biphenyl]-3-carbonyl azideAusbeute 119,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a vial (8 mL) diphenylphosphoryl azide (0.39 mL, 1.8 mmol) and triethylamine (0.25 mL, 1.8 mmol) were added to a stirred solution of biphenyl-3-carboxylic acid (0.30 g, 1.5 mmol) in isopropanol (3 mL). The vial was closed with a lid, and the reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated, and water (50 mL) was added. The mixture was extracted with ethyl acetate (3×50 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated to provide the title compound (0.40 g, 100%) was used in the next reaction without characterization or purification.

Aufarbeitung

  1. customThe vial was closed with a lid
  2. concentrationThe reaction mixture was concentrated
  3. additionwater (50 mL) was added
  4. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-59d10e76a5ef44edbf2561405cf89fbe
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09445594B2

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