Hydrochloric Acid → HCID 178441049, compound

HRID 1039575Notes

Reaction equation

HRID 1039575 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1Cl.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].[OH-].[Na+].Cl>O.CS(C)=O.ClC1C=CC=CC=1Cl>[Cl:8][C:6]1[N:5]=[N:4][C:3]([O:20][C:17]2[CH:18]=[CH:19][C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:15][CH:16]=2)=[C:2]([OH:1])[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73934-tert-ButylphenolHCID 14798Sodium HydroxideHCID 178516198HCID 178516198, compound

Product 1

HCID 178441049HCID 178441049, compoundYield 57.1%

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, 7.45 g (49.1 mmol) of 4-t-butylphenol, 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. The solids were dried under nitrogen gas for 24 hours, and then 25 mL of methyl t-butyl ether was added to the solids to obtain a slurry. After stirring for 1.5 hour, the obtained slurry was subjected to filtration, and the resultant solids were dried under a reduced pressure to obtain 2.61 g of 6-chloro-3-(4-t-butylphenoxy)-4-pyridazinol in the form of pale brown solids (yield: 57.2%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe deposited solids were taken out by filtration
  3. customThe solids were dried under nitrogen gas for 24 hours
  4. addition25 mL of methyl t-butyl ether was added to the solids
  5. customto obtain a slurry
  6. filtrationthe obtained slurry was subjected to filtration
  7. customthe resultant solids were dried under a reduced pressure

Sources & evidence

ORD record
ord-cfadea66bfee47f9ae5d21fc6e459897
Source dataset
uspto-grants-2013_10
Patent number
US08552182B2

Reaction notes

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