Hydrochloric Acid → HCID 178516202, compound

HRID 1039576Notes

Reaction equation

HRID 1039576 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1Cl.[F:10][C:11]([F:20])([F:19])[C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.[OH-].[Na+].Cl>O.CS(C)=O.ClC1C=CC=CC=1Cl>[Cl:8][C:6]1[N:5]=[N:4][C:3]([O:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:10])([F:19])[F:20])[CH:13]=2)=[C:2]([OH:1])[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73763-(Trifluoromethyl)phenolHCID 14798Sodium HydroxideHCID 178516198HCID 178516198, compound

Product 1

HCID 178516202HCID 178516202, compoundYield 69.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

3.0 g (purity: 90%; 16.4 mmol) of 4-hydroxy-3,6-dichloropyridazine, 7.96 g (49.1 mmol) of 3-trifluoromethylphenol, and 2.03 g (purity: 97%; 49.1 mmol) of sodium hydroxide were added to a mixture of 19.1 g of 1,2-dichlorobenzene and 3.0 g of dimethyl sulfoxide and matured at 180° C. for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and 50 g of pure water was added to the cooled mixture. A 35% aqueous hydrochloric acid solution was added to the resultant mixture so that the pH of the aqueous phase was adjusted to 2.1, and then the deposited solids were taken out by filtration. 25 mL of methyl t-butyl ether was added to the solids to obtain a slurry. The resultant solids were dried under a reduced pressure to obtain 3.32 g of 6-chloro-3-[3-(trifluoromethyl)phenoxy]-4-pyridazinol in the form of pale brown solids (yield: 69.7%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe deposited solids were taken out by filtration
  3. addition25 mL of methyl t-butyl ether was added to the solids
  4. customto obtain a slurry
  5. customThe resultant solids were dried under a reduced pressure

Sources & evidence

ORD record
ord-bf0f5a3caee14c29bf5aa96c94733cd6
Source dataset
uspto-grants-2013_10
Patent number
US08552182B2

Reaction notes

Loading…