3-Chloro-6-(3-methoxy-4-propoxyphenyl)pyridazine → HCID 57191541, compound

HRID 2254555Notes

Reaction equation

HRID 2254555 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)=[CH:6][CH:7]=1.[N:20]#[C:21][NH2:22].[Na]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:21]([NH:22][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)=[CH:6][CH:7]=1)#[N:20]

Participants

5

Reactant 2

HCID 193854943-Chloro-6-(3-methoxy-4-propoxyphenyl)pyridazineHCID 57375518Cyanamidnatrium

Product 1

HCID 57191541HCID 57191541, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

1.8 g 3-chloro-6-(3-methoxy-4-n-propoxyphenyl)pyridazine, 0.8 g sodium cyanamide and 3.6 g tetrabutylammonium chloride are boiled under reflux in 30 ml dry toluene for 5 hours. The reaction mixture is then evaporated in vacuo and the residue is boiled up briefly with 200 ml 2 N sodium hydrogen sulphate solution, while stirring thoroughly, the reaction product precipitating as a fine crystalline precipitate. The precipitate is filtered off with suction, washed with water and dried in vacuo. For purification, it is boiled up briefly with 50 ml isopropanol, filtered off with suction and dried in vacuo. This gives 1.5 g (83.3%) of the title compound of m.p. 187° C.

Workup

  1. customThe reaction mixture is then evaporated in vacuo
  2. customthe reaction product precipitating as a fine crystalline precipitate
  3. filtrationThe precipitate is filtered off with suction
  4. washwashed with water
  5. customdried in vacuo
  6. customFor purification, it
  7. filtrationfiltered off with suction
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e53a373310f0488eb6e4dd1e711822e1
Source dataset
uspto-grants-1993_08
Patent number
US05236918

Reaction notes

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