m-Chloroperbenzoic acid → 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfinyl)ethyl]-1-naphthalenecarboxamide

HRID 1958870Notes

Reaction equation

HRID 1958870 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2([C:42]([F:45])([F:44])[F:43])[O:24][N:23]=[C:22]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([C:35]([NH:37][CH2:38][CH2:39][S:40][CH3:41])=[O:36])=[CH:27][CH:26]=3)[CH2:21]2)[CH:16]=[C:17]([Cl:19])[CH:18]=1>ClCCl>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2([C:42]([F:43])([F:45])[F:44])[O:24][N:23]=[C:22]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([C:35]([NH:37][CH2:38][CH2:39][S:40]([CH3:41])=[O:6])=[O:36])=[CH:27][CH:26]=3)[CH2:21]2)[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 685153614-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylthio)ethyl]-1-naphthalenecarboxamide2×

Product 1

HCID 685128164-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfinyl)ethyl]-1-naphthalenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-74 °C

Procedure

m-Chloroperoxybenzoic acid (47 mg, 70% purity) was added at −78° C. to a stirred solution of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylthio)ethyl]-1-naphthalenecarboxamide (i.e. the product of Example 1, Step D, 100 mg) in dichloromethane (10 mL). The reaction mixture was stirred at −78 to −70° C. for 2.5 h, then quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane. The organic extract was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to provide the title compound (102 mg), a compound of this invention, as a white solid. 1H NMR (CDCl3): δ 8.78 (d, 1H), 8.29 (d, 1H), 7.42-7.64 (m, 7H), 7.37 (br t, 1H), 4.23 (d, 1H), 4.00 (q, 2H), 3.88 (d, 1H), 3.18 (dt, 1H), 2.89 (dt, 1H), 2.62 (s, 3H).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-891646412c2c4d488be7de6c211aa830
Source dataset
uspto-grants-2013_04
Patent number
US08410153B2

Reaction notes

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