Water → 2-Ethyl-6-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazine

HRID 1589461Notes

Reaction equation

HRID 1589461 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[CH:6][CH:7]=1.O>NC(CC)CO>[CH2:6]([C:5]1[N:4]=[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)=[N:4][N:3]2[CH:8]=1)[CH3:7]

Participants

4

Reactant 2

HCID 962WaterHCID 124495523-Chloro-6-[3-(trifluoromethyl)phenyl]pyridazine

Product 1

HCID 202465672-Ethyl-6-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 221292-Amino-1-butanolSolvent

Procedure

A 2.58 g sample of 3-chloro-6-[3-(trifluoromethyl)phenyl]pyridazine in 3.56 g of 2-amino-1-butanol was heated at 120° C. (internal temperature) for 18 hours, cooled and poured into cold water. The mixture was extracted with dichloromethane and the extracts washed with water, dried over anhydrous sodium sulfate and concentrated. The residue in ethyl acetate was chromatographed on silica gel with ethyl acetate to give 2.2 g of yellow oil. Crystallization from dichloromethane-hexane gave 2-{[6-[3-(trifluoromethyl)phenyl]-3-pyridazinyl]amino}-1-butanol as crystals, mp 84°-87° C.

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with dichloromethane
  3. washthe extracts washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue in ethyl acetate was chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-2d8f46115af044c68d9b8ec912423530
Source dataset
uspto-grants-1986_02
Patent number
US04569934

Reaction notes

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