Water → HCID 58136934, compound

HRID 217693Notes

Reaction equation

HRID 217693 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[C:4]([CH3:10])[C:3]=1[CH2:11][CH3:12].[N:13]#[C:14]Br.O.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[Cl:1][C:2]1[C:3]([CH2:11][CH3:12])=[C:4]([CH3:10])[C:5]2[N:6]([C:14]([NH2:13])=[N:9][N:8]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 55279275HCID 55279275, compound

Product 1

HCID 58136934HCID 58136934, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

(6-Chloro-5-ethyl-4-methylpyridazin-3-yl)hydrazine (W3.007; 340 mg) was dissolved in ethanol/water (10/2 ml) at RT while stirring. Thereafter, cyanogen bromide (386 mg, dissolved in 5 ml of ethanol and 1 ml of water) was cautiously added dropwise. After stirring at RT for 5 h, the mixture was left to stand overnight and then 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. 385 mg of the title compound were obtained. LC-MS rt: 0.62 min [M+H]+: 212.1 (met. b)

Workup

  1. stirringAfter stirring at RT for 5 h
  2. waitthe mixture was left
  3. extractionwas extracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationafter filtering off the desiccant,
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c5897c519605439db77b81f6e98011f5
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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