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

HRID 2045037Notes

Reaction equation

HRID 2045037 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-e9aa0734b3b541309de885bfaa84ff38
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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