m-Chloroperbenzoic acid → HCID 18980920, compound

HRID 482601Notes

Reaction equation

HRID 482601 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][C:15]([CH3:20])(C(=O)C)[C:14]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1.ClC1C=[C:33](C=CC=1)[C:34]([O:36]O)=[O:35]>C(Cl)Cl.C(OCC)C>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([N:12]2[CH2:16][C:15]([CH3:20])([O:36][C:34](=[O:35])[CH3:33])[C:14]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:13]2)=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 18980928HCID 18980928, compound

Product 1

HCID 18980920HCID 18980920, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 2.0 g (4.7 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-methyl-4-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 13a) in 10 ml of methylene chloride was added 2 g (9.8 mmole) of 85% 3-chloroperoxybenzoic acid (MCPBA). After standing for 72 hours at room temperature an additional 0.6 g of MCPBA was added and the reaction was let stand an additional 72 hours. The reaction mixture was diluted with diethyl ether, washed with dilute aqueous sodium bisulfite, dilute aqueous sodium bicarbonate, and brine. The resulting solution was dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and crystallized from diethyl ether and hexanes to yield the title compound, a white solid, mp 92°-96° C.

Workup

  1. waitthe reaction was let stand an additional 72 hours
  2. washwashed with dilute aqueous sodium bisulfite, dilute aqueous sodium bicarbonate, and brine
  3. dry with materialThe resulting solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customcrystallized from diethyl ether and hexanes

Sources & evidence

ORD record
ord-0da64dc5955a482b91646b0a6c8efa8d
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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