m-Chloroperbenzoic acid → HCID 59296173, compound

HRID 2233587Notes

Reaction equation

HRID 2233587 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([S:20][CH3:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:40])C=1.[Na]>ClCCl>[CH2:1]([C:5]1[N:6]=[C:7]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:26][CH:27]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([S:20]([CH3:21])=[O:40])[CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 5360545SodiumHCID 59296147HCID 59296147, compound

Product 1

HCID 59296173HCID 59296173, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 200 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methylsulfanyl-benzonitrile (prepared according to the method described in example 23) in 4 ml of dichloromethane at 0° C. was added 74 mg of meta-chloroperbenzoic acid. The resulting mixture was stirred at 0° C. for 2 hours then kept in the freezer overnight. A saturated aqueous solution of sodium hydrogenocarbonate was added and the organic layer was separated. The aqueous layer was extracted with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 203 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methylsulfinyl-benzonitrile, which was transformed into 3-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methylsulfinyl-phenyl}-4H-[1,2,4]oxadiazol-5-one according to the method described in example 1.

Workup

  1. customat 0° C.
  2. customthen kept in the freezer overnight
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25902d4db73c41cdb67a2e0438217b7d
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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