Phthaloyl chloride → HCID 22940047, compound

HRID 2424318Notes

Reaction equation

HRID 2424318 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=1[OH:16])=[O:10].N12CCN(CC1)CC2.[C:27](Cl)(=[O:37])[C:28]1[C:29](=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:30](Cl)=[O:31].[Cl:39][C:40]1[N:45]=[N:44][C:43]([O:46][C:47]2[C:52]([CH3:53])=[CH:51][CH:50]=[CH:49][C:48]=2[CH:54]2[CH2:56][CH2:55]2)=[C:42]([OH:57])[CH:41]=1>C(#N)C>[C:27]([O:57][C:42]1[CH:41]=[C:40]([Cl:39])[N:45]=[N:44][C:43]=1[O:46][C:47]1[C:52]([CH3:53])=[CH:51][CH:50]=[CH:49][C:48]=1[CH:54]1[CH2:56][CH2:55]1)(=[O:37])[C:28]1[C:29](=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:30]([O:16][C:15]1[N:14]([CH3:17])[N:13]=[C:12]([CH3:18])[C:11]=1[C:9](=[O:10])[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])=[O:31]

Participants

6

Reactant 4

HCID 6955Phthaloyl chlorideHCID 9237DabcoHCID 178424441HCID 178424441, compoundHCID 178434070HCID 178434070, compound

Product 1

HCID 22940047HCID 22940047, compoundYield 5.61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile (3 mL) was suspended 207 mg (0.726 mmol) of (2,4-dichlorophenyl)(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)methanone, 81.6 mg (0.729 mmol) of 1,4-diazabicyclo[2.2.2]octane was added to the suspension and the resulting mixture was stirred. To the mixture was added 105 ìL (0.729 mmol) of phthaloyl dichloride, and after stirring at room temperature for 1 hour, 200 mg (0.722 mmol) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was further added, and the resulting mixture was stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Daisogel 1001W, hexane:ethyl acetate, gradient) to obtain 28.0 mg (0.0405 mmol, Yield: 5.61%) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl phthalate (Compound No. 1625) and 163 mg (0.238 mmol, Yield: 33.0%) of bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]phthalate (Compound No. 2838).

Workup

  1. additionwas added to the suspension
  2. stirringafter stirring at room temperature for 1 hour
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour and 30 minutes
  4. extractionextracted with ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customthe obtained residue was purified by silica gel column chromatography (Daisogel 1001W, hexane:ethyl acetate, gradient)

Sources & evidence

ORD record
ord-4ecf182bf10f4c3ca516ac4aa3c28d6b
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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