3,6-Dichloropyridazine → 1-(2-Methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinylamino)ethylamino]-2-propanol

HRID 745509Notes

Reaction equation

HRID 745509 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH2:5][CH:6]([OH:14])[CH2:7][NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][NH2:11].[Cl:19][C:20]1[N:21]=[N:22][C:23](Cl)=[CH:24][CH:25]=1>C1C=CC=CC=1>[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH2:5][CH:6]([OH:14])[CH2:7][NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][NH:11][C:23]1[N:22]=[N:21][C:20]([Cl:19])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 673313,6-DichloropyridazineHCID 100607882-Propanol, 1-[(2-amino-1,1-dimethylethyl)amino]-3-(2-methylphenoxy)-

Product 1

HCID 100217191-(2-Methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinylamino)ethylamino]-2-propanolYield 67.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
110 °C

Procedure

To 1.58 g of 1-(2-methylphenoxy)-3-(1,1-dimethyl-2-aminoethylamino)-2-propanol heated at 110° C. in an oil bath with stirring was added 934 mg of 3,6-dichloropyridazine little by little. After heating at 110° C. for 1 hour, the reaction mixture was dissolved in benzene, and extracted with 1N hydrochloric acid. The aqueous layer was made alkaline with potassium carbonate, and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated to give 1.55 g of 1-(2-methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinylamino)ethylamino]-2-propanol as an oil.

Workup

  1. extractionextracted with 1N hydrochloric acid
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-10f16b323fc24e5990ae31f32d0b0969
Source dataset
uspto-grants-1986_07
Patent number
US04599333

Reaction notes

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