Acetonitrile → 4-(3-(2,6-Dichlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-methoxy-N-(4-(methylsulfonyl)phenyl)benzamide

HRID 508973Notes

Reaction equation

HRID 508973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:31]=[CH:30][C:18]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25](SC)=[CH:24][CH:23]=3)=[O:20])=[C:17]([O:32][CH3:33])[CH:16]=2)[N:10]=1.[C:34](#N)C.O[O:38][S:39]([O-:41])=O.[K+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:31]=[CH:30][C:18]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([S:39]([CH3:34])(=[O:41])=[O:38])=[CH:24][CH:23]=3)=[O:20])=[C:17]([O:32][CH3:33])[CH:16]=2)[N:10]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfiteHCID 1364924304-(3-(2,6-Dichlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-methoxy-N-(4-(methylthio)phenyl)benzamide

Product 1

HCID 1369486174-(3-(2,6-Dichlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-methoxy-N-(4-(methylsulfonyl)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-(3-(2,6-dichlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-methoxy-N-(4-(methylthio)phenyl)benzamide (Intermediate-38, 0.070 g, 0.13 mmol) in mixture of acetonitrile:water (3 mL:3 mL) was added oxone (0.053 g, 0.34 mmol). The reaction mass was stirred at RT for 24 h. The reaction mass was diluted with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.020 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.18 (s, 3H), 3.94 (s, 3H), 7.68-7.76 (m, 7H), 7.80 (d, J=8.7 Hz, 1H), 7.90 (d, J=8.7 Hz, 1H), 7.99 (d, J=8.4 Hz, 1H), 10.48 (s, 1H), 12.76 (br s, 1H); MS (m/z): 531.14 (M+H)+.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-de38dedc0ea34d3fbdefb81a389541f8
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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