Chloroacetaldehyde → 6,8-Dichloroimidazo[1,2-b]pyridazine

HRID 1969100ノート

反応式

HRID 1969100 の反応式
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8].[CH:10](O)(C)[CH3:11].ClCC=O>O>[Cl:9][C:5]1[CH:6]=[C:7]([Cl:8])[C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[N:4]=1

参加物

5

反応物 3

HCID 33ChloroacetaldehydeHCID 3776IsopropanolHCID 577867894,6-dichloropyridazin-3-amine

生成物 1

HCID 575175396,8-Dichloroimidazo[1,2-b]pyridazine収率 87%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-amino-4,6-dichloropyridazine (0.315 g, 1.92 mmol), 3 mL of isopropanol and 0.5 mL of a 50% chloroacetaldehyde in water solution was stirred at 80° C. for 20 h, then concentrated to remove isopropanol. The resulting yellow mixture was treated with 10 mL of a saturated aq. NaHCO3 solution and extracted with two 10 mL portions of dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to a yellow oil. Column chromatography (0->33% EtOAc/hexanes) afforded 0.313 g (87%) of 6,8-dichloro-imidazo[1,2-b]pyridazine as a light yellow solid.

後処理

  1. concentrationconcentrated
  2. customto remove isopropanol
  3. additionThe resulting yellow mixture was treated with 10 mL of a saturated aq. NaHCO3 solution
  4. extractionextracted with two 10 mL portions of dichloromethane
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow oil

出典と根拠

ORDレコード
ord-9c9a4425adae4a9d8f4cc359974e11ad
出典データセット
uspto-grants-2013_04
特許番号
US08426441B2

反応ノート

読み込み中…