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

HRID 1045185Notes

Reaction equation

HRID 1045185 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].O>O1CCCC1>[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

6

Reactant 4

HCID 962WaterHCID 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 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Tetrahydro-2H-pyran-4-yl)methanol (2.0 g) in tetrahydrofuran (20 mL) was treated with 60% NaH (1.377 g). The mixture was stirred for 20 minutes at the room temperature. To this mixture 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% HC1, 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-e67350b1750c4fec817459210c08d1e0
Source dataset
uspto-grants-2013_10
Patent number
US08563735B2

Reaction notes

Loading…