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

HRID 2356022ノート

反応式

HRID 2356022 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21863450Trifluoroacetic acid methylene chloride溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-c966e3af7f11413191a095a41d265862
出典データセット
uspto-grants-2010_07
特許番号
US07754886B2

反応ノート

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