m-Chloroperbenzoic acid → HCID 59296139, compound

HRID 2233588Notes

Reaction equation

HRID 2233588 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[S:8][C:9]=1[CH2:10][S:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:38])C=1.[Na]>ClCCl>[CH2:1]([C:5]1[N:6]=[C:7]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=2)[S:8][C:9]=1[CH2:10][S:11]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)=[O:38])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 5360545SodiumHCID 59296183HCID 59296183, compound

Product 1

HCID 59296139HCID 59296139, compoundYield 89.2%

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-ylmethylsulfanyl]-benzonitrile (prepared according to the method described in example 14) in 4 ml of dichloromethane at 0° C. was added 80 mg of meta-chloroperbenzoic acid. The resulting mixture was stirred at 0° C. for 5 hours, at room temperature for 2 hours than kept in the fridge 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. The crude product was purified by column chromatography on silica gel (gradient of 1 to 4% acetone/dichloromethane) to give 185 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethylsulfinyl]-benzonitrile, which was transformed into 3-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethanesulfinyl]-phenyl}-4H-[1,2,4]oxadiazol-5-one according to the method described in example 1.

Workup

  1. customat 0° C.
  2. customthan kept in the fridge 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
  8. customThe crude product was purified by column chromatography on silica gel (gradient of 1 to 4% acetone/dichloromethane)

Sources & evidence

ORD record
ord-050b9df9f0c84af69a3758b20d7a7eef
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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