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

HRID 1969100노트

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HRID 1969100 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c9a4425adae4a9d8f4cc359974e11ad
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426441B2

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