Cyanogen Bromide → HCID 58136913, compound

HRID 657915Notes

Reaction equation

HRID 657915 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[N:13][C:12]([NH:15][NH2:16])=[CH:11][C:10]=1[CH:17]([CH3:19])[CH3:18].[N:20]#[C:21]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.CCO.O>[Cl:8][C:9]1[C:10]([CH:17]([CH3:19])[CH3:18])=[CH:11][C:12]2[N:13]([C:21]([NH2:20])=[N:16][N:15]=2)[N:14]=1

Participants

7

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 86650808HCID 86650808, compound

Product 1

HCID 58136913HCID 58136913, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 19096565Water ethanolSolvent

Procedure

(6-Chloro-5-isopropylpyridazin-3-yl)hydrazine trifluoroacetic acid salt (W3.013; 400 mg) was initially charged in ethanol/water (6/1 ml) at RT while stirring. Thereafter, cyanogen bromide (353 mg, dissolved in a mixture of 1 ml of EtOH and 0.5 ml of water) was cautiously added dropwise. After stirring for 5 hours, the mixture was left to stand overnight and stirred for a further day. After standing overnight, the solvent was drawn off and the residue was admixed with water. Once the residue had been alkalized with saturated potassium carbonate solution, it was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after filtering off the desiccant, dried under reduced pressure. 400 mg of the title compound were obtained in sufficient purity.

Workup

  1. additionwas cautiously added dropwise
  2. stirringAfter stirring for 5 hours
  3. waitthe mixture was left
  4. stirringstirred for a further day
  5. waitAfter standing overnight
  6. extractionwas extracted three times with dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationafter filtering off the desiccant,
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e1bb0d1885514000800752291a322fe7
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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