Water → HCID 58045769, compound

HRID 657908Notes

Reaction equation

HRID 657908 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[N:13][C:12]([NH:15][NH2:16])=[C:11]([CH2:17][CH3:18])[CH:10]=1.O.[N:20]#[C:21]Br>CCO.CCO.O>[Cl:8][C:9]1[CH:10]=[C:11]([CH2:17][CH3:18])[C:12]2[N:13]([C:21]([NH2:20])=[N:16][N:15]=2)[N:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 86650803HCID 86650803, compound

Product 1

HCID 58045769HCID 58045769, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Procedure

(6-Chloro-4-ethylpyridazin-3-yl)hydrazine trifluoroacetate (W3.003; 1.35 g) were initially charged in EtOH (25 ml) and water (4 ml) while stirring at RT. Thereafter, cyanogen bromide (997 mg), dissolved in EtOH/water (5/2 ml), was cautiously added dropwise. After stirring at RT for 8 h and standing overnight, the mixture was stirred at 55° C. for another 4 h. Subsequently, the solvent was concentrated and the residue was admixed with water. Once it had been alkalized with saturated potassium carbonate solution, the mixture was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 918 mg of the title compound were obtained.

Workup

  1. additionwas cautiously added dropwise
  2. waitstanding overnight
  3. stirringthe mixture was stirred at 55° C. for another 4 h
  4. concentrationSubsequently, the solvent was concentrated
  5. extractionthe mixture was extracted three times with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationafter the desiccant had been filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-20bcf0610c4344e6afb6b04b4d1ac512
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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