Trifluoroacetic acid → HCID 66710870, Verbindung

HRID 1805634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805634
[N:1]1([C:10](=[N:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:11]2[C:16](=[O:17])[CH:15]=[CH:14][N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[N:12]=2)C2C=CC=CC=2[N:3]=[N:2]1.[N-]=[N+]=[N-].[Na+].FC(F)(F)C(O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[C:29]1([N:28]2[C:10]([C:11]3[C:16](=[O:17])[CH:15]=[CH:14][N:13]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[N:12]=3)=[N:1][N:2]=[N:3]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

7

Edukt 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 59436266HCID 59436266, Verbindung

Produkt 1

HCID 66710870HCID 66710870, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-[1H-benzotriazol-1-yl(phenylimino)methyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.094 g, 0.20 mmol), sodium azide (0.030 g, 0.46 mmol), and tetrabutylammonium bromide (0.015 g, 0.047 mmol) in methylene chloride (5 mL) and water (5 mL) was treated with trifluoroacetic acid (0.040 mL, 0.52 mmol) and stirred 24 h at room temperature. After that time, the organic layer was separated and the aqueous layer was extracted with methylene chloride (3×25 mL). The combined organic extracts were washed with saturated NaCl aqueous solution (50 mL), dried (MgSO4), and concentrated. The crude product purified by flash column chromatography (silica gel, 80:20 hexanes/ethyl acetate to ethyl acetate) to give an off-white solid that was recrystallized from ethyl acetate/hexanes to give 0.034 g (56%) of 3-(1-phenyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one as colorless crystals.

Aufarbeitung

  1. customAfter that time, the organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride (3×25 mL)
  3. washThe combined organic extracts were washed with saturated NaCl aqueous solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product purified by flash column chromatography (silica gel, 80:20 hexanes/ethyl acetate to ethyl acetate)
  7. customto give an off-white solid
  8. customthat was recrystallized from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a3a3a2f6a0a74830843a9edfbd4e7ed3
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354411B2

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