Benzenesulfonyl chloride → HCID 67953961, compound

HRID 1916857Notes

Reaction equation

HRID 1916857 reaction equation
[Cl:1][C:2]1[N:6]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].[H-].[Na+].[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[C:18]([O:17][C:16]([N:15]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:14])[F:13])=[CH:7][N:6]2[C:2]=1[Cl:1])[S:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:33])=[O:32])=[O:22])([CH3:19])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 90090789HCID 90090789, compound

Product 1

HCID 67953961HCID 67953961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 9-C (0.100 g, 0.300 mmol) in DMF (5 mL) at room temperature was added 60% NaH (0.012 g, 0.300 mmol) and the reaction mixture was stirred for 10 minutes. Benzenesulfonyl chloride (0.053 g, 0.300 mmol) was added and the reaction mixture was stirred at room temperature overnight. DMF was removed in vacuo and water and methylene chloride were added. The organic layer was washed with H2O (2×), brine, dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure to afford the crude product. The crude material was purified by flash column chromatography (SiO2) eluting with a gradient of 0-100% ethyl acetate in hexane to afford compound 9-D (0.040 g, 28%); MS m/z (M+H+) 476.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customDMF was removed in vacuo and water and methylene chloride
  3. additionwere added
  4. washThe organic layer was washed with H2O (2×), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customto afford the crude product
  9. customThe crude material was purified by flash column chromatography (SiO2)
  10. washeluting with a gradient of 0-100% ethyl acetate in hexane
  11. customto afford compound 9-D (0.040 g, 28%)

Sources & evidence

ORD record
ord-5bedaaa55bf846a391692beadb8b1d84
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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