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

HRID 270523ノート

反応式

HRID 270523 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 86604839N'-(4-azido-1-phenylbutylidene)-5-chloro-2-methyl benzohydrazide収率 59.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-96468bcf6b4644da860f53fe8bcb7cc2
出典データセット
uspto-grants-2008_11
特許番号
US07449486B2

反応ノート

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