Water → HCID 59261367、化合物

HRID 643676

反応式

HRID 643676 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1/[CH:4]=[N:5]/[NH2:6].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([CH3:25])[N:19]=1.O>C1(C)C=CC=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1/[CH:4]=[N:5]/[NH:6][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([CH3:25])[N:19]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 9629214(e)-(2-Chlorobenzylidene)hydrazineHCID 119590832,4-Dichloro-6-methylpyridine

生成物 1

HCID 59261367HCID 59261367、化合物収率 31.4%

試薬・触媒・溶媒 2

HCID 53485975CID 53485975触媒HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

(E)-1-(2-chlorobenzylidene)hydrazine (0.351 g, 2.27 mmol), dichloro[1,1′bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.0185 g, 0.0227 mmol) and potassium carbonate (0.471 g, 3.41 mmol) was added to a 50-mL RBF. Toluene (2 mL) was added and 2,4-dichloro-6-methylpyridine (0.368 g, 2.27 mmol) in 3 mL of toluene was added. The red mixture was heated to 100° C. After 18 h, the reaction was allowed to cool to RT and water (20 mL) was added. The mixture was filtered and 190 mg of (E)-1-(2-chlorobenzylidene)-2-(4-chloro-6-methylpyridin-2-yl) hydrazine was collected as a tan solid. The filtrate was absorbed on silica gel and purified by silica gel chromatography (8/2 hexanes/DCM to 7/2/1 hexans/DCM/EtOAc) to afford an additional 200 mg of (E)-1-(2-chlorobenzylidene)-2-(4-chloro-6-methylpyridin-2-yl) hydrazine as a tan solid. MS (ESI, pos. ion) m/z: 280.0 (M+1).

後処理

  1. temperatureto cool to RT
  2. filtrationThe mixture was filtered
  3. custom190 mg of (E)-1-(2-chlorobenzylidene)-2-(4-chloro-6-methylpyridin-2-yl) hydrazine was collected as a tan solid
  4. customThe filtrate was absorbed on silica gel
  5. custompurified by silica gel chromatography (8/2 hexanes/DCM to 7/2/1 hexans/DCM/EtOAc)

出典と根拠

ORDレコード
ord-18f87604d6eb4ec6913459692f7693df
出典データセット
uspto-grants-2010_04
特許番号
US07700593B2

関連ノート

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