Isopropanol → HCID 59834466, compound

HRID 1157261Notes

Reaction equation

HRID 1157261 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][OH:22])[CH:5]=[C:6]([Cl:19])[C:7]=1[S:8][C:9]1[N:10]=[N:11][C:12]([Cl:18])=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=1.CC(C)=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O.C(OCC)(=O)C.O>[Cl:19][C:6]1[CH:5]=[C:4]([CH2:20][C:21]([OH:25])=[O:22])[CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[N:10]=[N:11][C:12]([Cl:18])=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=1

Participants

7

Reactant 3

HCID 3776IsopropanolHCID 59834489HCID 59834489, compoundHCID 131709961Jones' reagent

Product 1

HCID 59834466HCID 59834466, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenyl]-ethanol (74) (100 mg, 0.26 mmol) in acetone (2.0 mL) cooled to 0° C. was treated with a 2.7M solution of Jones reagent (0.21 mL, 0.57 mmol, prepared via standard method). The reaction was stirred at 0° C. for 1.25 h. At this time, the reaction was treated with 2-propanol until the red solution turned green. This mixture was then diluted with ethyl acetate (50 mL) and water (25 mL). The organics were separated, dried with magnesium sulfate, filtered, and concentrated under vacuum to afford [3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenyl]-acetic acid (75) (92.5 mg, 89%) as an off-white foam. This material was used without further purification; LRMS-APCI for C15H13Cl3N2O2S (M+H)+ at m/z=390. Exact Mass=389.9763; Molecular weight=391.71

Workup

  1. customThe organics were separated
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-74bb0545dac341c58291aa316117a411
Source dataset
uspto-grants-2010_10
Patent number
US07807674B2

Reaction notes

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