Water → 4-Fluorobenzoic acid 2-[6-(trifluoromethyl)-2-pyridinyl]hydrazide

HRID 1598952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1598952
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[C:7]([NH:9][NH2:10])[CH:6]=[CH:5][CH:4]=1.[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C.O>C1COCC1>[F:12][C:2]([F:1])([F:11])[C:3]1[N:8]=[C:7]([NH:9][NH:10][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:14]([F:13])=[CH:15][CH:16]=2)[CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 133393842-Hydrazinyl-6-(trifluoromethyl)pyridine

Produkt 1

HCID 676387304-Fluorobenzoic acid 2-[6-(trifluoromethyl)-2-pyridinyl]hydrazideAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-(trifluoromethyl)pyridin-2-ylhydrazine (3.00 g, 16.4 mmol) and 4-fluorobenzoyl chloride (2.95 g, 18.63 mmol) in anhydrous THF (20 mL) at 0° C. under N2 was added diisopropylethylamine (2.41 g, 18.63 mmol). After 15 min, the solution was allowed to warm to room temperature over 1 h. Water (80 mL) was added, and the aqueous layer was extracted with ethyl acetate (2×100 mL). The organic extracts were combined, washed with water (100 mL), dried over MgSO4, and concentrated in vacuo to a tan solid. Recrystallization from ethyl acetate afforded the title compound of Step A as a white solid (3.16 g). 1H NMR (Me2SO-d6, 400 MHz) δ10.55 (s,1H), 9.10 (s, 1H), 8.00 (m,2H), 7.80 (t, 1H), 7.40 (t,2H), 7.15 (d, 1H), 6.90 (d, 1H).

Aufarbeitung

  1. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  2. washwashed with water (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo to a tan solid
  5. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a58c2e91749645178b984b5afd229705
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739326

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