Water → HCID 21099456, compound

HRID 2376943Notes

Reaction equation

HRID 2376943 reaction equation
NC(N)=[O:3].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])(=[O:29])=[O:28])=[CH:23][N:22]=1.O>ClCCl>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])(=[O:29])=[O:28])=[CH:23][N+:22]=1[O-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 21099457HCID 21099457, compound

Product 1

HCID 21099456HCID 21099456, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Urea-hydrogen peroxide (0.36 g, 3.83 mmol) was suspended in dichloromethane (3 mL) and trifluoroacetic anhydride (0.77 g, 3.67 mmol) was added to form a clear solution. 2-Chloro-5-[(2-fluorophenyl)sulfonyl]pyridine (Example 1 Steps 1 and 2, 0.5 g, 1.84 mmol) in dichloromethane (1 mL) was added and the reaction stirred at room temperature under nitrogen for 7 hours. The mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium thiosulfate (×3). The combined aqueous layers were extracted once with ethyl acetate, then the combined organic layers washed again with sodium thiosulfate then with brine, dried over MgSO4 and concentrated in vacuo to give 2-chloro-5-[(2-fluorophenyl)sulfonyl]pyridine 1-oxide as a pale yellow solid (0.53 g, quant.). δH (500 MHz, d6 DMSO): 8.84 (1H, d, J=1.5 Hz), 8.08 (1H, td, J=7.5, 1.5 Hz), 8.03 (1H, d, J=8.6 Hz), 7.87-7.77 (2H, m), 7.51 (1H, q, J=8 Hz), 7.47 (1H, d, J=8.6 Hz); m/z (ES+) 288[MH+].

Workup

  1. customto form a clear solution
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with saturated aqueous sodium thiosulfate (×3)
  4. extractionThe combined aqueous layers were extracted once with ethyl acetate
  5. washthe combined organic layers washed again with sodium thiosulfate
  6. dry with materialwith brine, dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f68b98729064a6c95cb9909c72090b3
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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