Triethylamine → Tert-butyl 2-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)hydrazinecarboxylate

HRID 1257408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257408
Cl[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:7]=1.[NH:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH2:19].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([C:6]2[N:7]=[C:3]([CH2:2][NH:19][NH:18][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[S:4][CH:5]=2)[CH:13]=[CH:12][CH:11]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 629239612-(Chloromethyl)-4-[3-(trifluoromethyl)phenyl]-1,3-thiazole

Produkt 1

HCID 66939173Tert-butyl 2-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)hydrazinecarboxylateAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound (0.60 g) obtained in Example 103b was dissolved in N,N-dimethylformamide (3 mL), and tert-butyl hydrazinecarboxylate (1.45 g) and triethylamine (0.61 mL) were added. The reaction mixture was stirred at room temperature for 96 hr, and diluted with ethyl acetate and water. The ethyl acetate layer was separated, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give tert-butyl 2-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)hydrazinecarboxylate (0.54 g) as a colorless solid. The solid was dissolved in 10% hydrogen chloride-ethanol (30 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was washed with diisopropyl ether to give the title compound (0.45 g) as colorless crystals.

Aufarbeitung

  1. customThe ethyl acetate layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c6c7fc9ac25f4ffaad6ce45710317889
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461348B2

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