Water → HCID 58244274, compound

HRID 389131Notes

Reaction equation

HRID 389131 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([C:15]1[N:19]([CH3:20])[C:18]([C:21]2[CH:26]=[CH:25][C:24](F)=[CH:23][C:22]=2[C:28]([F:31])([F:30])[F:29])=[N:17][N:16]=1)([CH3:14])[CH3:13])[C:5]([NH2:7])=[O:6].[CH3:32][S-:33].[Na+].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([CH3:14])([C:15]1[N:19]([CH3:20])[C:18]([C:21]2[CH:26]=[CH:25][C:24]([S:33][CH3:32])=[CH:23][C:22]=2[C:28]([F:31])([F:30])[F:29])=[N:17][N:16]=1)[CH3:13])[C:5]([NH2:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 58243897HCID 58243897, compound

Product 1

HCID 58244274HCID 58244274, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-bromo-4-(1-{5-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-4H-1,2,4-triazol-3-yl}-1-methylethoxy}benzamide (300 mg) was dissolved in DMF (6 ml), and sodium thiomethoxide (210 mg) was added thereto, followed by stirring at room temperature for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid was washed with ethyl acetate to obtain, as a white solid, 3-bromo-4-(1-methyl-1-{4-methyl-5-[4-(methylsulfanyl)-2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl}ethoxy]benzamide (163 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-1268afd78f6e44e590a9571dd3a8498b
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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