1-Tetralone → 4-[(2E)-2-(3,4-dihydro-2H-naphthalen-1-ylidene)hydrazinyl]-3-nitrobenzenesulfonamide

HRID 1785767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785767
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH:12][C:13](OC(C)(C)C)=O)=[C:7]([N+:20]([O-:22])=[O:21])[CH:6]=1)(=[O:4])=[O:3].[C:23]1(=O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30]C=2)[CH2:26][CH2:25][CH2:24]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)(C(F)(F)F)=O.ClCCl>[C:13]1(=[N:12]/[NH:11][C:8]2[CH:9]=[CH:10][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:6][C:7]=2[N+:20]([O-:22])=[O:21])/[CH2:30][CH2:29][CH2:28][C:27]2[C:32]/1=[CH:23][CH:24]=[CH:25][CH:26]=2

Komponenten

5

Edukt 3

HCID 107241-TetraloneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22730367Tert-butyl 2-(4-(aminosulfonyl)-2-nitrophenyl)hydrazinecarboxylate

Produkt 1

HCID 96121654-[(2E)-2-(3,4-dihydro-2H-naphthalen-1-ylidene)hydrazinyl]-3-nitrobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

A room temperature solution of Example 73A (145 mg,0.44 mmol) in 1:1 TFA/dichloromethane (10 mL) was stirred for 4 hours and concentrated. The concentrate was dissolved in ethanol (2 mL), treated with 3,4-dihydro-1(2H)-naphthalenone (8.2 mg, 0.06 mmol) and pyridinium p-toluenesulfonate (2 mg, 0.008 mmol), heated to reflux, stirred for 2 hours, cooled to room temperature, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane to provide the desired product. MS (ESI(−)) m/e 359 (M−H)−.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in ethanol (2 mL)
  3. temperatureheated
  4. temperatureto reflux
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e8120fa171c24b559a2c6215295f49b4
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504512B2

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