Hydrochloric Acid → HCID 59834470, compound

HRID 271211Notes

Reaction equation

HRID 271211 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([SH:9])=[C:4]([Cl:10])[CH:3]=1.[Cl:11][C:12]1[N:13]=[N:14][C:15](Cl)=[CH:16][C:17]=1[CH:18]([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Cl:8][C:6]1[CH:7]=[C:2]([NH2:1])[CH:3]=[C:4]([Cl:10])[C:5]=1[S:9][C:15]1[N:14]=[N:13][C:12]([Cl:11])=[C:17]([CH:18]([CH3:20])[CH3:19])[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 140241623,6-Dichloro-4-isopropylpyridazineHCID 198673824-Amino-2,6-dichlorobenzene-1-thiol

Product 1

HCID 59834470HCID 59834470, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-amino-2,6-dichloro-benzenethiol (82) (1.0 g, 5.2 mmol) in N,N-dimethylformamide at 25° C. was treated with 3,6-dichloro-4-isopropyl-pyridazine (7) (990 mg, 5.2 mmol) and potassium carbonate (2.16 g, 15.6 mmol). The resulting mixture was heated to 90° C. for 18 h. At this time, the reaction was cooled to 25° C., poured onto a mixture of ice water and a 1N aqueous hydrochloric acid solution (10 mL). The resulting solution was brought to pH=7 with additional 1N aqueous hydrochloric acid solution and then was extracted with ethyl acetate (2×100 mL). The organics were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 petroleum ether/ethyl acetate) afforded 3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenylamine (83) (1.29 g, 72%) as an off-white foam; ES(+)-HRMS m/e calcd for C13H12Cl3N3S (M+H)+ 347.9891, found 347.9889. Exact Mass=346.9817; Molecular weight=348.68

Workup

  1. temperatureAt this time, the reaction was cooled to 25° C.
  2. extractionwas extracted with ethyl acetate (2×100 mL)
  3. washThe organics were washed with a saturated aqueous sodium chloride solution (1×50 mL)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-10c12fe6892742edbaec9ffbda4dd968
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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