Sodium Dithionite → HCID 178466115, compound

HRID 552864Notes

Reaction equation

HRID 552864 reaction equation
CS[CH2:3][CH2:4][C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([C:14]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:31])[C:27]([F:30])([F:29])[F:28])=[C:21]([C:32]([F:35])([F:34])[F:33])[CH:20]=4)[O:16][N:15]=3)=[CH:13][C:7]=2[N:6]=1.[CH:36]1C=C([Cl:42])C=C(C(OO)=O)C=1.[O-:47][S:48](S([O-])=O)=[O:49].[Na+].[Na+].Cl.CCOC(C)=O>ClCCl.CCOC(C)=O>[ClH:42].[CH3:36][S:48]([CH2:3][CH2:4][C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([C:14]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:31])[C:27]([F:28])([F:29])[F:30])=[C:21]([C:32]([F:35])([F:33])[F:34])[CH:20]=4)[O:16][N:15]=3)=[CH:13][C:7]=2[N:6]=1)(=[O:49])=[O:47]

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 70297m-Chloroperbenzoic acidHCID 21866389Hydrogen chloride-ethyl acetateHCID 178503671HCID 178503671, compound

Product 1

HCID 178466115HCID 178466115, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[2-(methylthio)ethyl]-5-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-benzimidazole (400 mg) in dichloromethane (8.0 ml) was added mCPBA (534 mg), followed by stirring at room temperature for 3 hours. To the reaction mixture was added a Na2S2O4 aqueous solution, followed by stirring for 1 hour. The reaction solution was extracted three times with EtOAc, and the organic layer was combined, dried over anhydrous MgSO4, filtered, and then concentrated. The residue was purified by silica gel chromatography (chloroform:CH3OH=10:1) to obtain a yellow oily substance. This was dissolved in EtOAc, and a 4M-HCl/EtOAc solution was added thereto, followed by concentration. The residue was washed with IPE to obtain 2-[2-(methylsulfonyl)ethyl]-5-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-benzimidazole hydrochloride (146 mg) as pale yellow powders.

Workup

  1. stirringby stirring for 1 hour
  2. extractionThe reaction solution was extracted three times with EtOAc
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (chloroform:CH3OH=10:1)
  7. customto obtain a yellow oily substance
  8. concentrationfollowed by concentration
  9. washThe residue was washed with IPE

Sources & evidence

ORD record
ord-4e6956af8a4d4b8ca07698a475644bfa
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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