m-Chloroperbenzoic acid → HCID 21091046, compound

HRID 351266Notes

Reaction equation

HRID 351266 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:26]=[CH:25][C:17]([O:18][CH2:19][CH2:20][NH:21][C:22]([NH2:24])=[O:23])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:27]([F:30])([F:29])[F:28])=[N:10]2)=[CH:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:26]=[CH:25][C:17]([O:18][CH2:19][CH2:20][NH:21][C:22]([NH2:24])=[O:23])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:27]([F:30])([F:28])[F:29])=[N:10]2)=[CH:5][CH:4]=1)=[O:39]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 21091048HCID 21091048, compound

Product 1

HCID 21091046HCID 21091046, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of N-(2-{4-[1-[4-(methylthio)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy}ethyl)urea (250 mg) and mCPBA (326 mg) in CH2Cl2 (10 ml) was stirred for 18 hrs. sat. NaHCO3 and CH2Cl2 was added. Aqueous layer was separated and extracted. The combined organic layer was washed with sat. NaHCO3 (twice), dried and evaporated to give 207 mg (79.9%) of crude product. The crude product was column chromatographed by preparative TLC to give 207 mg (80%) of N-(2-{4-[1-[4-(methylsulfinyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy}ethyl)urea as an amorphous.

Workup

  1. customAqueous layer was separated
  2. extractionextracted
  3. washThe combined organic layer was washed with sat. NaHCO3 (twice),
  4. customdried
  5. customevaporated
  6. customto give 207 mg (79.9%) of crude product
  7. customchromatographed by preparative TLC

Sources & evidence

ORD record
ord-14a18b1114f64ee69e7ee7eabd504f62
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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