Water → HCID 23629693、化合物

HRID 2375674

反応式

HRID 2375674 の反応式
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][N:8]=[C:9]([C:17]#[N:18])[C:10]([NH:12][CH2:13][CH:14]1[CH2:16][CH2:15]1)=[O:11].[Cl-].[Al+3].[Cl-].[Cl-].O.[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:18][C:17]1[C:3]2[C:2](=[C:1]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:6]=[CH:5][CH:4]=2)[N:7]=[N:8][C:9]=1[C:10]([NH:12][CH2:13][CH:14]1[CH2:16][CH2:15]1)=[O:11]

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 866130972-(biphenyl-2-yl-hydrazono)-2-cyano-N-cyclopropylmethylacetamide

生成物 1

HCID 23629693HCID 23629693、化合物収率 26.2%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

To a suspension of 2-(biphenyl-2-yl-hydrazono)-2-cyano-N-cyclopropylmethylacetamide (1.9 g, 6.0 mmol) in anhydrous toluene (30 mL) was added aluminum chloride (1.72 g, 13.0 mmol). The mixture was heated at 70° C. for 1 hour, cooled to room temperature, and diluted with ethyl acetate (150 mL). Water was added dropwise until no further precipitate formed. Aqueous 10% sodium hydroxide (150 mL) was added and the layers were separated. The organic layer was washed with 10% sodium hydroxide (100 mL), water (100 mL), and brine (100 mL) and dried over sodium sulfate, filtered, and concentrated to a semisolid. The material was dissolved in chloroform and purified on silica gel to give 500 mg of material which was then recrystallized from ethyl acetate/hexanes and then from hot toluene (two times) to afford the pure product as a solid (117 mg, 6.2%). 1H NMR (500.133 MHz, CDCl3) δ 9.23 (t, J=5.3 Hz, 1H), 9.13 (bs, 1H), 8.43 (d, J=8.4 Hz, 1H), 8.17 (bs, 1H), 7.86 (d, J=7.1 Hz, 1H), 7.81 (td, J=7.7, 1.2 Hz, 1H), 7.71 (d, J=7.5 Hz, 2H), 7.49 (t, J=7.3 Hz, 2H), 7.43 (td, J=7.2, 0.9 Hz, 1H), 3.23 (t, J=6.3 Hz, 2H), 1.12 (t, J=5.6 Hz, 1H), 0.45 (dd, J=6.5, 1.5 Hz, 2H), 0.29 (d, J=4.4 Hz, 2H). MS APCI, m/z=319 (M+H). HPLC 1.83 min.

後処理

  1. temperaturecooled to room temperature
  2. customformed
  3. customthe layers were separated
  4. washThe organic layer was washed with 10% sodium hydroxide (100 mL), water (100 mL), and brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a semisolid
  8. dissolutionThe material was dissolved in chloroform
  9. custompurified on silica gel

出典と根拠

ORDレコード
ord-c2f2bac84537451b92273a6a2fbda283
出典データセット
uspto-grants-2008_12
特許番号
US07465795B2

関連ノート

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