2,2,2-Trifluoroethanol → 6-Chloro-3-(2,2,2-trifluoroethoxy)pyridazin-4-amine

HRID 1025946Notes

Reaction equation

HRID 1025946 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[NH2:8].[CH2:10]([OH:15])[C:11]([F:14])([F:13])[F:12].O.[OH-].[Li+]>CS(C)=O.O>[Cl:9][C:5]1[N:4]=[N:3][C:2]([O:15][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:7]([NH2:8])[CH:6]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 168937Lithium hydroxide, monohydrateHCID 2984983,6-Dichloropyridazin-4-amine

Product 1

HCID 866631346-Chloro-3-(2,2,2-trifluoroethoxy)pyridazin-4-amineYield 84.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 3.28 g 3,6-dichloro-pyridazin-4-ylamine in 30 mL dimethylsulfoxide and 4.0 g trifluoroethanol was added 1.84 g lithium hydroxide hydrate and 3 mL water and the mixture was heated to 80° C. for 18 h. The reaction mixture was diluted with 100 mL water and stirred at ambient temperature for 2 h. The resulting solid was collected by filtration washed with water and dried to constant weight under high vacuum to yield 3.84 g of the title compound as off white crystals, MS 228.1 and 230.1 (M+H)+.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-103efccd225e4e069ede0997f6fc81fd
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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