Diisopropylethylamine → tert-Butyl 2-(2-fluoro-4-nitrobenzoyl)-2-methylhydrazinecarboxylate

HRID 56608

Reaktionsgleichung

Reaktionsgleichung von HRID 56608
F[B-](F)(F)F.N1(O[C+](N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[F:32][C:33]1[CH:41]=[C:40]([N+:42]([O-:44])=[O:43])[CH:39]=[CH:38][C:34]=1[C:35]([OH:37])=O.[CH3:45][NH:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49]>CN(C=O)C>[F:32][C:33]1[CH:41]=[C:40]([N+:42]([O-:44])=[O:43])[CH:39]=[CH:38][C:34]=1[C:35]([N:46]([CH3:45])[NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[O:37]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 3026792-Fluoro-4-nitrobenzoic acidHCID 15671306N'-methyl(tert-butoxy)carbohydrazideHCID 178484679HCID 178484679, Verbindung

Produkt 1

HCID 117622795tert-Butyl 2-(2-fluoro-4-nitrobenzoyl)-2-methylhydrazinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Under argon and at RT, 17.1 g (53.4 mmol, 1.3 eq.) of (benzotriazol-1-yloxy)bisdimethylaminomethylium fluoroborate and 21.4 ml (123.1 mol, 3.0 eq.) of N,N-diisopropylethylamine were added to a solution of 9.1 g (49.3 mmol, 1.2 eq.) of 2-fluoro-4-nitrobenzoic acid in 200 ml of DMF, and the mixture was stirred at RT for 20 min. A solution of 12.5 g (purity 48%, 41 mmol) of tert-butyl 2-methylhydrazinecarboxylate in 50 ml of DMF was added, and the reaction mixture was stirred at RT for 6 h. After removal of the DMF under reduced pressure and addition of water/ethyl acetate and phase separation, the organic phase was washed with 10% aqueous citric acid and with saturated aqueous sodium chloride solution, dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures). Yield: 8.35 g (65% of theory)

Aufarbeitung

  1. stirringthe reaction mixture was stirred at RT for 6 h
  2. customAfter removal of the DMF
  3. additionunder reduced pressure and addition of water/ethyl acetate and phase separation
  4. washthe organic phase was washed with 10% aqueous citric acid and with saturated aqueous sodium chloride solution
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures)

Quellen und Nachweise

ORD-Eintrag
ord-66727fb3bd2e4db498f2326358c3bab4
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434690B2

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