Dimethyl Sulfoxide → HCID 178424441, compound

HRID 1039585Notes

Reaction equation

HRID 1039585 reaction equation
[CH:1]1([C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=2[O-:6])[CH2:3][CH2:2]1.[Na+].CS(C)=O.[OH:17][C:18]1[CH:23]=[C:22]([Cl:24])[N:21]=[N:20][C:19]=1Cl.C1(C2C=CC=C(C)C=2O)CC1>C1CCCCC1.O>[Cl:24][C:22]1[N:21]=[N:20][C:19]([O:6][C:5]2[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:4]=2[CH:1]2[CH2:3][CH2:2]2)=[C:18]([OH:17])[CH:23]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 229399512-Cyclopropyl-6-methylphenolHCID 68107637Sodium 2-cyclopropyl-6-methylphenoxideHCID 178516198HCID 178516198, compound

Product 1

HCID 178424441HCID 178424441, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent

Procedure

To a mixture of 29.8 g (purity: 93.6%; 163 mmol) of sodium 2-cyclopropyl-6-methylphenoxide and 5 g of dimethyl sulfoxide was added 10.0 g (purity: 90%; 54.6 mmol) of 4-hydroxy-3,6-dichloropyridazine at room temperature. Then, the resultant mixture was heated from room temperature to 140° C. to effect a reaction for 28 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and 300 g of pure water and 200 g of cyclohexane were added to the cooled mixture, and stirred for 30 minutes, and an organic phase containing 2-cyclopropyl-6-methylphenol added in an excess amount was separated. Then, the resultant aqueous phase containing a sodium salt of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was quantitatively determined by an HPLC internal standard analysis method, which showed that 13.3 g of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 87.9%) and 60.4 mg of 3-chloro-6-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 0.4%) were obtained.

Workup

  1. customa reaction for 28 hours
  2. customAfter completion of the reaction
  3. additionadded in an excess amount
  4. customwas separated
  5. additionThen, the resultant aqueous phase containing a sodium salt of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol

Sources & evidence

ORD record
ord-aed26c7ebeab4a5ca1357f055c9e7be0
Source dataset
uspto-grants-2013_10
Patent number
US08552182B2

Reaction notes

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