Dimethyl Sulfate → HCID 135731737, compound

HRID 972774Notes

Reaction equation

HRID 972774 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[OH:15])=[CH:6][CH:7]=1.S(OC)(O[CH3:20])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:20])=[CH:10][C:9]=2[OH:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 135731740HCID 135731740, compound

Product 1

HCID 135731737HCID 135731737, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

i. 3-Chloro-6-(2,4-dihydroxyphenyl)pyridazine (4.0 g, 0.18 mole), dimethyl sulphate (2.55 g, 0.0201 mole), potassium carbonate (10.0 g, 0.072 mole) and dry acetone (100 ml) were stirred at room temperature for 20 hours. The reaction mixture was filtered and the inorganic residue was washed with more acetone. Evaporation of the combined filtrates gave a brown residue which was extracted wth dilute sodium hydroxide solution. The aqueous extract was washed with dichloromethane, treated with charcoal, filtered and acidified. The resulting precipitate was collected, washed with water and crystallised from ethanol to give 3-chloro-6-(2-hydroxy-4-methoxyphenyl)-pyridazine (2.2 g, 49%; m.p. 156°-157°).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe inorganic residue was washed with more acetone
  3. customEvaporation of the combined filtrates
  4. customgave a brown residue which
  5. extractionwas extracted wth dilute sodium hydroxide solution
  6. extractionThe aqueous extract
  7. washwas washed with dichloromethane
  8. additiontreated with charcoal
  9. filtrationfiltered
  10. customThe resulting precipitate was collected
  11. washwashed with water
  12. customcrystallised from ethanol

Sources & evidence

ORD record
ord-f4802101251a434eb85bd3ab179242de
Source dataset
uspto-grants-1977_10
Patent number
US04053601

Reaction notes

Loading…