Hydrochloric Acid → HCID 59834489, compound

HRID 271205Notes

Reaction equation

HRID 271205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][OH:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[SH:8].[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][C:19]=1[CH:20]([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][OH:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[S:8][C:17]1[N:16]=[N:15][C:14]([Cl:13])=[C:19]([CH:20]([CH3:22])[CH3:21])[CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 140241623,6-Dichloro-4-isopropylpyridazineHCID 59834437HCID 59834437, compound

Product 1

HCID 59834489HCID 59834489, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-(3,5-dichloro-4-mercapto-phenyl)-ethanol (73) (620 mg, 2.78 mmol) in dimethyl sulfoxide (25 mL) was treated with 3,6-dichloro-4-isopropyl-pyridazine (7) (530 mg, 2.78 mmol) and potassium carbonate (1.54 g, 11.12). The resulting mixture was heated to 90° C. for 18 h. At this time, the reaction was cooled to 25° C., poured into a solution of water (200 mL) and a 1N aqueous hydrochloric acid solution (25 mL). The mixture was extracted with ethyl acetate (2×200 mL). The organics were then washed with water (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried with magnesium sulfate, filtered, and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 70:30 petroleum ether/ethyl acetate) afforded 2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenyl]-ethanol (74) (550 mg, 52%) as a pale yellow oil; EI(+)-HRMS m/e calcd for C15H15Cl3N2OS (M+H)+ 377.0044, found 377.0043. Exact Mass=375.9971; Molecular weight=377.72

Workup

  1. temperatureAt this time, the reaction was cooled to 25° C.
  2. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  3. washThe organics were then washed with water (1×100 mL)
  4. dry with materiala saturated aqueous sodium chloride solution (1×100 mL), dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b8954b1f062c4553b5516bf49adef067
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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