Bromoacetone → 2-Methyl-6-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazine hydrobromide

HRID 1589468Notes

Reaction equation

HRID 1589468 reaction equation
[NH2:1][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.[Br:18][CH2:19][C:20](=O)[CH3:21]>C(O)C>[BrH:18].[CH3:21][C:20]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:17])[F:16])[CH:9]=3)=[N:4][N:3]2[CH:19]=1

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 135653673-Amino-6-(3-trifluoromethylphenyl)pyridazine

Product 1

HCID 135653662-Methyl-6-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazine hydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1.5 g sample of 3-amino-6-[3-(trifluoromethyl)phenyl]pyridazine, 1.23 g of bromoacetone and 50 ml of ethanol was refluxed for 18 hours. The volatiles were removed in vacuo and the residue dissolved in dichloromethane. The solution was treated with activated carbon, filtered, and concentrated. The residue was crystallized from dichloromethane-hexane to give 1.0 g of the desired product as cream colored crystals, mp 219°-221° C.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. additionThe solution was treated with activated carbon
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-ebc16b882c6f455cae49408f6a73502d
Source dataset
uspto-grants-1986_02
Patent number
US04569934

Reaction notes

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