hydroxylamine-O-sulfonic acid → 4-(2-Pyridin-3-yl-4-trifluoromethyl-imidazol-1-yl)-benzenesulfonamide

HRID 52370Notes

Reaction equation

HRID 52370 reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=[C:15]2[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6].[N+:31](CCCC)(CCCC)(CCCC)CCCC.[F-].C([O-])(=O)C.[Na+].NOS(O)(=O)=O>C1COCC1.O.C(OCC)(=O)C>[CH3:1][Si:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[N:16]=[C:15]2[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:12][CH:13]=1)(=[O:6])=[O:7].[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:15]2[N:14]([C:11]3[CH:12]=[CH:13][C:8]([S:5]([NH2:31])(=[O:7])=[O:6])=[CH:9][CH:10]=3)[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=2)[CH:24]=1

Participants

9

Reactant 4

HCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 105276743-[1-[4-[[2-(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

Product 2

HCID 97993874-(2-Pyridin-3-yl-4-trifluoromethyl-imidazol-1-yl)-benzenesulfonamideYield 173.5%HCID 105276743-[1-[4-[[2-(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[1-[4-[[2(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol -2-yl]pyridine was prepared from Example 30 with a method similar to that described in Example 48, Step 1. To a solution of 3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (0.200 g, 0.46 mmol) in 1.0 mL of dry THF was added n-Bu4NF (1.38 mL of 1.0H THF solution, 1.38 mmol). The mixture was heated to reflux for 1 hour and cooled to room temperature. A solution of sodium acetate (0.17 g, 2.1 mmol) in 3 mL of water and hydroxylamine-O-sulfonic acid (0.26 g, 2.3 mmol) were added sequentially and the mixture was stirred for 1 hour. Water (7 mL) and ethyl acetate (7 mL) were added. The organic phase was separated and washed with saturated NaHCO3 solution, water, brine, dried over HgSO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to give 0.147 g of 4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (87%): mp(DSC) 213°-215 ° C. Anal. Calc'd. for C15H11F3N4O2S: C, 48.91; H, 3.01; N, 15.21; S, 8.71. Found: C, 48.58; H, 2.99; N, 14.87; S, 8.85.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe organic phase was separated
  4. washwashed with saturated NaHCO3 solution, water, brine
  5. dry with materialdried over HgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

Sources & evidence

ORD record
ord-d2a7222710944de9a90e8ba21d5528f2
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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