p-Toluenesulfonic acid monohydrate → N'-(4-azido-1-phenylbutylidene)-5-chloro-2-methyl benzohydrazide

HRID 512908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512908
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([NH:9][NH2:10])=[O:8].[N:13]([CH2:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O)=[N+:14]=[N-:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:13]([CH2:16][CH2:17][CH2:18][C:19](=[N:10][NH:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[CH3:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[N+:14]=[N-:15]

Komponenten

6

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 108779184-AzidobutyrophenoneHCID 131576295-Chloro-2-methylbenzohydrazide

Produkt 1

HCID 86604839N'-(4-azido-1-phenylbutylidene)-5-chloro-2-methyl benzohydrazideAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-2-methylbenzohydrazide (2.70 g, 14.62 mmol) prepared as in Example 1, Step B, in toluene (100 mL) was added 4-azido-1-phenylbutan-1-one (3.04 g, 16.1 mmol) prepared as in Example 70, Step A, followed by p-toluenesulfonic acid monohydrate (0.28 g, 1.46 mmol). The reaction was heated to reflux and stirred under a Dean-Stark trap for 16 hours. The cooled mixture was diluted with EtOAc (300 mL) and washed with NaHCO3 (100 mL). The aqueous layer was extracted with EtOAc (100 mL) and the combined organics were washed with brine (100 mL), dried over Na2SO4 and concentrated. The residue was triturated with ether and filtered to afford the product (3.09 g, 59%) as a tan solid.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. washwashed with NaHCO3 (100 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (100 mL)
  5. washthe combined organics were washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was triturated with ether
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-cb343a2fd5114b72883ea8b1fa64c143
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102639B2

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