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 59481Notes

Reaction equation

HRID 59481 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-b5a4d36aabee402e82b6f693b88ed81a
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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