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

HRID 1353001Notes

Reaction equation

HRID 1353001 reaction equation
C[S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]2[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:26][Si:27]([CH3:55])([CH3:54])[CH2:28][CH2:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[N:41]=[C:40]2[C:48]2[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=2)=[CH:35][CH:34]=1)(=[O:32])=[O:31].[N+:56](CCCC)(CCCC)(CCCC)CCCC.[F-].C([O-])(=O)C.[Na+].NOS(O)(=O)=O>C1COCC1.O.C(OCC)(=O)C>[CH3:26][Si:27]([CH3:55])([CH3:54])[CH2:28][CH2:29][S:30]([C:33]1[CH:34]=[CH:35][C:36]([N:39]2[CH:43]=[C:42]([C:44]([F:45])([F:46])[F:47])[N:41]=[C:40]2[C:48]2[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=2)=[CH:37][CH:38]=1)(=[O:31])=[O:32].[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:12]2[N:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([NH2:56])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=2)[CH:21]=1

Participants

10

Reactant 5

HCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 9929140HCID 9929140, compoundHCID 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 87%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 with the product of Example 28 with a method similar to that described in Example 45, 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 1.0 M 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 MgSO4 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 MgSO4
  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-b6e10e9b9be147319f200186f2f7ea69
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

Loading…