Dabco → HCID 23014035, compound

HRID 2424319Notes

Reaction equation

HRID 2424319 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]1([S:37](Cl)(=[O:39])=[O:38])[CH:32]=[CH:31][CH:30]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:28]=1.[Cl:41][C:42]1[N:47]=[N:46][C:45]([O:48][C:49]2[C:54]([CH3:55])=[CH:53][CH:52]=[CH:51][C:50]=2[CH:56]2[CH2:58][CH2:57]2)=[C:44]([OH:59])[CH:43]=1>C(#N)C.O>[C:27]1([S:37]([O:59][C:44]2[CH:43]=[C:42]([Cl:41])[N:47]=[N:46][C:45]=2[O:48][C:49]2[C:54]([CH3:55])=[CH:53][CH:52]=[CH:51][C:50]=2[CH:56]2[CH2:58][CH2:57]2)(=[O:39])=[O:38])[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([O:16][C:15]2[N:14]([CH3:17])[N:13]=[C:12]([CH3:18])[C:11]=2[C:9](=[O:10])[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])(=[O:34])=[O:35])[CH:28]=1

Participants

7

Reactant 4

HCID 9237DabcoHCID 962401,3-Benzenedisulfonyl dichlorideHCID 178424441HCID 178424441, compoundHCID 178434070HCID 178434070, compound

Product 1

HCID 23014035HCID 23014035, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In acetonitrile (4 mL) was suspended 122 mg (0.428 mmol) of (2,4-dichlorophenyl)(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)methanone, 72.0 mg (0.643 mmol) of 1,4-diazabicyclo[2.2.2]octane, then 117 mg (0.425 mmol) of 1,3-benzenedisulfonyl dichloride were added to the suspension in an ice bath, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was ice-cooled, and further 100 mg (0.361 mmol) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was added to the mixture, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane:ethyl acetate, gradient) to obtain 135 mg (0.177 mmol, Yield: 49.0%) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl 1,3-benzenedisulfonate (Compound No. 2333) and 38.0 mg (0.0503 mmol, Yield: 13.9%) of bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]1,3-benzenedisulfonate (Compound No. 3755).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane:ethyl acetate, gradient)

Sources & evidence

ORD record
ord-8ee7c6c018534a55a7454ae42698d6d1
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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