18-Crown-6 → HCID 57095529, compound

HRID 2254557Notes

Reaction equation

HRID 2254557 reaction equation
Br[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[C:10]([O:19][CH3:20])[CH:9]=2)=[CH:6][CH:7]=1.[N:21]#[C:22][NH2:23].[Na].C1OCCOCCOCCOCCOCCOC1>CC(CC(=O)C)C>[C:22]([NH:23][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[C:10]([O:19][CH3:20])[CH:9]=2)=[CH:6][CH:7]=1)#[N:21]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 19742760HCID 19742760, compoundHCID 57375518Cyanamidnatrium

Product 1

HCID 57095529HCID 57095529, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

3 g 3-bromo-6[4-(2-methylpropoxy)-3-methoxyphenyl]pyridazine, 1.3 g sodium cyanamide and 0.5 g 18-crown-6 are boiled under reflux in 30 ml 2-methyl-4-pentanone for 5 hours. The reaction solution is then evaporated in vacuo and the residue is boiled up briefly with 200 ml 2N sodium hydrogen sulphate solution, while stirring thoroughly, the reaction product precipitating as a fine crystalline precipitate. The precipitate is filtered off with suction and boiled up again with isopropanol, the mixture is cooled and the product is filtered off with suction and, after washing with isopropanol and petroleum spirit (b.p. 50°-70° C.), dried in vacuo. This gives 2.5 g (80.6%) of the title compound of m.p. 191° C.

Workup

  1. customThe reaction solution is then evaporated in vacuo
  2. customthe reaction product precipitating as a fine crystalline precipitate
  3. filtrationThe precipitate is filtered off with suction
  4. temperaturethe mixture is cooled
  5. filtrationthe product is filtered off with suction
  6. washafter washing with isopropanol and petroleum spirit (b.p. 50°-70° C.)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b83d7e7018f14e418e4afccb46b86df3
Source dataset
uspto-grants-1993_08
Patent number
US05236918

Reaction notes

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