3-(2-Amino-2-methylpropoxy)-6-chloropyridazine → 1-(2-Chloro-5-methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinyloxy)ethylamino)-2-propanol

HRID 745495Notes

Reaction equation

HRID 745495 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[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:16]=1[O:17][CH2:18][CH:19]1[O:21][CH2:20]1>C(O)C>[Cl:14][C:15]1[CH:25]=[CH:24][C:23]([CH3:26])=[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 130128362-[(2-Chloro-5-methylphenoxy)methyl]oxirane

Product 1

HCID 100010281-(2-Chloro-5-methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinyloxy)ethylamino)-2-propanolYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.6 g of 3-(2-amino-2-methylpropoxy)-6-chloropyridazine obtained in Example 1 (a) and 5.0 g of 1-(2-chloro-5-methylphenoxy)-2,3-epoxypropane in 50 ml of ethanol was refluxed for 4 hours. The solvent was evaporated under reduced pressure a solution of the residue in 100 ml of benzene was extracted with 30 ml of 10% hydrochloric acid. The aqueous layer was made alkaline with 10% sodium hydroxide and extracted with chloroform, and the organic layer was dried over magnesium sulfate. The solvent was evaporated and the residue was chromatographed on a column of Florisil (50 g) using chloroform as an eluent. From the eluate was obtained 5.7 g of 1-(2-chloro-5-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 a solution of the residue in 100 ml of benzene
  2. extractionwas extracted with 30 ml of 10% hydrochloric acid
  3. extractionextracted with chloroform
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on a column of Florisil (50 g)

Sources & evidence

ORD record
ord-fe9e3748ca3e43b0aafd072f73dc2bc2
Source dataset
uspto-grants-1986_07
Patent number
US04599333

Reaction notes

Loading…