Isopropanol → 4-Isopropoxy-3-nitro-benzenesulfonamide

HRID 2403035Notes

Reaction equation

HRID 2403035 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[Na].F[C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18]>C1COCC1.CC(O)C>[CH:1]([O:4][C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 5360545Sodium2×HCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 696690644-Isopropoxy-3-nitro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

A solution of isopropanol (225 mL) and small chunks of sodium metal (1.92 g, 83.6 mmol) were heated to reflux for 2.5 hours, until the sodium was consumed. The resulting solution was added while still hot to a solution of 4-fluoro-3-nitro-benzenesulfonamide (8.37 g, 38.0 mmol, example 2, step b) in THF/iPrOH (1/1, v/v, 150 mL) over a 10 minute period and stirred at room temperature for 3.5 hours. The reaction mixture was partitioned between EtOAc and brine and 1 N aqueous HCl. The organic phase was then washed with brine, dried with Na2SO4 and evaporated to give the title compound.

Workup

  1. customwas consumed
  2. customThe reaction mixture was partitioned between EtOAc and brine and 1 N aqueous HCl
  3. washThe organic phase was then washed with brine
  4. dry with materialdried with Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-a7de07bd8e4444ec9cdad13f8b7e172d
Source dataset
uspto-grants-2014_08
Patent number
US08798939B2

Reaction notes

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