3-(2-Amino-2-methylpropoxy)-6-chloropyridazine → 1-(2-Chloro-3-methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinyloxy)ethylamino]-2-propanol

HRID 745494Notes

Reaction equation

HRID 745494 reaction equation
[NH2:1][C:2]([CH3:13])([CH3:12])[CH2:3][O:4][C:5]1[N:6]=[N:7][C:8]([Cl:11])=[CH:9][CH:10]=1.[Cl:14][C:15]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:16]=1[O:17][CH2:18][CH:19]1[O:21][CH2:20]1>CO>[Cl:14][C:15]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:16]=1[O:17][CH2:18][CH:19]([OH:21])[CH2:20][NH:1][C:2]([CH3:13])([CH3:12])[CH2:3][O:4][C:5]1[N:6]=[N:7][C:8]([Cl:11])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 103304683-(2-Amino-2-methylpropoxy)-6-chloropyridazineHCID 233133352-[(2-Chloro-3-methylphenoxy)methyl]oxirane

Product 1

HCID 99783091-(2-Chloro-3-methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinyloxy)ethylamino]-2-propanolYield 66.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6.04 g of 3-(2-amino-2-methylpropoxy)-6-chloropyridazine obtained in Example 1, (a) and 5.95 g of 1-(2-chloro-3-methylphenoxy)-2,3-epoxypropane in 120 ml of methanol was refluxed for 3 hours. The solvent was evaporated under reduced pressure. A solution of the residue in benzene was extracted with 175 ml of 0.2N hydrochloric acid. The aqueous layer was made alkaline with potassium carbonate and extracted with chloroform. The chloroform layer was dried over sodium sulfate. The solvent was evaporated and the residue (10 g) was purified by column chromatography (50 g of Florisil; eluted with chloroform) to give 7.98 g of 1-(2-chloro-3-methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinyloxy)ethylamino]-2-propanol as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionA solution of the residue in benzene was extracted with 175 ml of 0.2N hydrochloric acid
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform layer was dried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue (10 g) was purified by column chromatography (50 g of Florisil; eluted with chloroform)

Sources & evidence

ORD record
ord-d970a2615e1946218829aff55aee5dab
Source dataset
uspto-grants-1986_07
Patent number
US04599333

Reaction notes

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