m-Chloroperbenzoic acid → HCID 10168247, compound

HRID 1835368Notes

Reaction equation

HRID 1835368 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C:13]([CH3:41])([CH3:40])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([S:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.ClC1C=CC=C(C(OO)=[O:52])C=1>ClCCl>[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([C:13]([CH3:41])([CH3:40])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([S:31]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)=[O:52])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23502838HCID 23502838, compound

Product 1

HCID 10168247HCID 10168247, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 130 mg (0.210 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(3-methoxy-phenylsulfanyl)-4-o-tolyl-pyridin-3-yl]-N-methyl-isobutyramide (Example 103) in 1 ml dichloromethane a solution of 52 mg (0.21 mmol) 3-chloroperbenzoic acid in 1.5 ml dichloromethane was added at 0° C. After completed addition the reaction mixture was allowed to warm to room temperature and stirred over night. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium carbonate solution. The aqueous layer was extracted with three portions of dichloromethane. The combined organic layers were dried with sodium sulfate and concentrated. Column chromatography afforded 9 mg (7%) of the title compound as a colorless viscous oil.

Workup

  1. additionaddition the reaction mixture
  2. washwashed with saturated aqueous sodium carbonate solution
  3. extractionThe aqueous layer was extracted with three portions of dichloromethane
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-34c84bfdf2ef4bd3a7fb92ef3f411f42
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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