Tetrahydrofuran → HCID 18543965, compound

HRID 1268064Notes

Reaction equation

HRID 1268064 reaction equation
[C:1]1([C:7]2[S:8][C:9]([C:12]3[NH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=3)=[N:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+:26](CCCC)(CCCC)CCCC)CCC.O.O.O.[C:42]([O-])(=O)[CH3:43].[Na+].N[O:48][S:49]([OH:52])(=O)=O.[CH2:53]1[CH2:57]O[CH2:55][CH2:54]1>O>[NH2:26][S:49]([C:42]1[CH:43]=[CH:57][C:53]([N:13]2[CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[N:16]=[C:12]2[C:9]2[S:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:11][N:10]=2)=[CH:54][CH:55]=1)(=[O:52])=[O:48]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 76284hydroxylamine-O-sulfonic acidHCID 2724141Tetrabutylammonium FluorideHCID 23665404Sodium Acetate TrihydrateHCID 178506254HCID 178506254, compound

Product 1

HCID 18543965HCID 18543965, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-[4- {(2-trimethyl silyl) ethyl)sulfonyl}phenyl]-2-[2-(phenyl)-1,3,4-thiadiazol-5-yl]-4-(trifluoromethyl)-1H-imidazole (2.3 g, 4.29 mmol) in dry THF (50 mL) was added tetrabutylammonium fluoride (12.8 mL, 1M solution in THF, 12.8 mmol). The mixture was refluxed for 30 min and cooled to room temperature. A solution of sodium acetate trihydrate (2.92 g, 21.4 mmol) in water (5 mL) was added followed by hydroxylamine-O-sulfonic acid (2.42 g, 21.4 mmol), and the mixture was stirred for 4 hour. The reaction mixture was quenched by adding water (50 mL) and extracted with ethyl acetate. The organic fractions were washed with water, brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography on silica gel using hexane/ethyl acetate as an eluent to give the product (1.2 g, 62%) as a white solid; 1H NMR δ (DMSO-d6) 8.54 (1H, s), 7.98 (4H, m), 7.87 (2H, d, J=8.7 Hz), 7.61 (2H, s), 7.58 (3H, m); 13C NMR δ (DMSO-d6) 170.7, 160.0, 147.0, 141.0, 140.1, 133.9, 133.7, 131.6, 130.9, 129.9, 129.6, 128.6, 124.0(q).

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. customThe reaction mixture was quenched
  3. additionby adding water (50 mL)
  4. extractionextracted with ethyl acetate
  5. washThe organic fractions were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3218d0adc1854b9d943c93b22be45855
Source dataset
uspto-grants-2003_04
Patent number
US06555563B1

Reaction notes

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