Ethanol → HCID 53856373, compound

HRID 2420448Notes

Reaction equation

HRID 2420448 reaction equation
[C:1]([C:3]1[N:4]=[N:5][C:6]([N:9]([CH3:11])[CH3:10])=[CH:7][CH:8]=1)#N.[OH2:12].[OH-].[Na+].[CH2:15]([OH:17])[CH3:16]>C(Cl)Cl>[CH3:11][N:9]([CH3:10])[C:6]1[N:5]=[N:4][C:3]([C:1]([O:17][CH2:15][CH3:16])=[O:12])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 21327996HCID 21327996, compound

Product 1

HCID 53856373HCID 53856373, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Ethyl (6-dimethylaminopyridazin-3-yl)-carboxylate can be obtained by heating a suspension of 3-cyano-6-dimethylaminopyridazine (52.7 g) in a mixture of distilled water (600 cc), 10N sodium hydroxide solution (200 cc) and ethanol (400 cc) at a temperature of about 70° C for 41/2 hours. After cooling to a temperature of about 20° C, methylene chloride (200 cc) is added to the reaction mixture which is allowed to stand for 12 hours at a temperature of about 20° C. The aqueous phase is decanted, acidified with 12N hydrochloric acid (150 cc), and evaporated to dryness under reduced pressure. Ethanol (360 cc), 1,2-dichloroethane (360 cc) and pure methane-sulphonic acid (76 g) are added to the residue thus obtained. The resulting mixture is then heated under reflux for 20 hours. After cooling to a temperature of about 20° C, the insoluble material which has formed is filtered off and washed with methylene chloride (3 × 20 cc). A saturated aqueous sodium carbonate solution (720 cc) is added to the filtrate thus obtained. The resulting insoluble product is filtered off and washed with methylene chloride (2 × 200 cc). The aqueous phase is decanted and washed with methylene chloride (2 × 100 cc). The combined organic fractions are dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure. Ethyl (6-dimethylaminopyridazin-3-yl)-carboxylate (50.81 g), melting at 112° C is thus obtained.

Workup

  1. temperatureby heating
  2. additionis added to the reaction mixture which
  3. customThe aqueous phase is decanted
  4. customevaporated to dryness under reduced pressure
  5. additionEthanol (360 cc), 1,2-dichloroethane (360 cc) and pure methane-sulphonic acid (76 g) are added to the residue
  6. customthus obtained
  7. temperatureThe resulting mixture is then heated
  8. temperatureunder reflux for 20 hours
  9. customthe insoluble material which has formed
  10. filtrationis filtered off
  11. washwashed with methylene chloride (3 × 20 cc)
  12. additionA saturated aqueous sodium carbonate solution (720 cc) is added to the filtrate
  13. customthus obtained
  14. filtrationThe resulting insoluble product is filtered off
  15. washwashed with methylene chloride (2 × 200 cc)
  16. customThe aqueous phase is decanted
  17. washwashed with methylene chloride (2 × 100 cc)
  18. dry with materialThe combined organic fractions are dried over magnesium sulphate
  19. filtrationfiltered
  20. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1cb62e7f446e48d08cc794641f0f8a8a
Source dataset
uspto-grants-1978_08
Patent number
US04110450

Reaction notes

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