Sodium hydride → 4-((1,4-Dioxan-2-yl)methoxy)-3-nitrobenzenesulfonamide

HRID 629617Notes

Reaction equation

HRID 629617 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][OH:8].[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]>O1CCCC1>[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][O:8][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]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 12655091(1,4-Dioxan-2-yl)methanolHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 671264774-((1,4-Dioxan-2-yl)methoxy)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1,4-Dioxan-2-yl)methanol (380 mg) in tetrahydrofuran (30 ml) was treated with sodium hydride (60%) (245 mg) at room temperature for 30 minutes. The reaction mixture was cooled in an ice bath and 4-fluoro-3-nitrobenzenesulfonamide (675 mg) was added. The resulting mixture was stirred at room temperature for 2 hours and another portion of sodium hydride (60%, 245 mg) was added. The reaction mixture was stirred overnight and quenched with ice water (3 ml). The cloudy mixture was filtered and the filtrate was concentrated. The residue was triturated with methanol to give the title compound.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. stirringThe reaction mixture was stirred overnight
  3. customquenched with ice water (3 ml)
  4. filtrationThe cloudy mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-e81ead4c2b5e4a06b71dd57c197096ce
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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