Water → HCID 59296147, compound

HRID 2233586Notes

Reaction equation

HRID 2233586 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=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](F)[CH:13]=1)[CH2:2][CH2:3][CH3:4].[CH3:31][S-:32].[Na+].O>CN(C)C=O>[CH2:1]([C:5]1[N:6]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=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:32][CH3:31])[CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 59296167HCID 59296167, compound

Product 1

HCID 59296147HCID 59296147, compoundYield 657.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 50 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-fluoro-benzonitrile (prepared according to the method described in example 1) in 10 ml of dimethylformamide was added 121 mg of sodium thiomethoxide. The resulting mixture was stirred at room temperature overnight, then poured into water, extracted with diisopropyl ether. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by crystallization from diisopropyl ether/heptane to give 350 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methylsulfanyl-benzonitrile, which was transformed into 3-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methylsulfanyl-phenyl}-4H-[1,2,4]oxadiazol-5-one according to the method described in example 1.

Workup

  1. extractionextracted with diisopropyl ether
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by crystallization from diisopropyl ether/heptane

Sources & evidence

ORD record
ord-9b849f9899454b00ac7f81c4f83188d9
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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