Cyanogen Bromide → HCID 58136793, compound

HRID 532344Notes

Reaction equation

HRID 532344 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])[C:10]=1[CH3:19].[N:20]#[C:21]Br.C(=O)([O-])[O-].[K+].[K+]>CCO.O>[Cl:8][C:9]1[C:10]([CH3:19])=[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 10476Cyanogen Bromide2×HCID 11430Potassium CarbonateHCID 86650804HCID 86650804, compound

Product 1

HCID 58136793HCID 58136793, compoundYield 112.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Procedure

(6-Chloro-4-ethyl-5-methylpyridazin-3-yl)hydrazine trifluoroacetic acid salt (W3.008; 340 mg) was initially charged in a mixture of EtOH (12 ml) and water (2 ml) at RT while stirring. Thereafter, cyanogen bromide (240 mg), dissolved in 3 ml of EtOH and 1 ml of water, was cautiously added dropwise and the mixture was stirred for 8 h. After standing overnight, 0.5 eq. cyanogen bromide solution was added and the mixture was stirred again at RT for 4.5 h and then at 55° C. for 2 h. After standing overnight, the solvent was drawn off 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. 270 mg of the title compound were obtained.

Workup

  1. stirringthe mixture was stirred for 8 h
  2. stirringthe mixture was stirred again at RT for 4.5 h
  3. waitat 55° C. for 2 h
  4. waitAfter standing overnight
  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-5bf9d40755334520ab8e7f75025e30ac
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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