Hydrochloric Acid → 3-nitro-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 1848868Notes

Reaction equation

HRID 1848868 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23].Cl>O1CCCC1.O>[N+:22]([C:13]1[CH:14]=[C:15]([S:18]([NH2:21])(=[O:19])=[O:20])[CH:16]=[CH:17][C:12]=1[O:8][CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)([O-:24])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 671264583-nitro-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(Tetrahydro-2H-pyran-4-yl)methanol (2.0 g) in tetrahydrofuran (20 mL) was treated with 60% NaH (1.377 g). The solution was stirred for 20 minutes at room temperature. To this solution was added 4-fluoro-3-nitrobenzenesulfonamide (2.84 g) portion-wise. The reaction was stirred for another 2 hours. The mixture was poured into water, neutralized with 10% HCl, and extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel eluting with 20%-60% ethyl acetate in hexanes.

Workup

  1. stirringThe reaction was stirred for another 2 hours
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with flash column chromatography on silica gel eluting with 20%-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-17635a4ae662487387c0c4c33da34a5f
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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