Isopropanol → 4-Isopropoxy-N-methyl-3-nitrobenzenesulfonamide

HRID 536040Notes

Reaction equation

HRID 536040 reaction equation
[H-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].F[C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH3:18])(=[O:16])=[O:15])=[CH:10][C:9]=1[N+:19]([O-:21])=[O:20].CCOC(C)=O>O>[CH3:18][NH:17][S:14]([C:11]1[CH:12]=[CH:13][C:8]([O:6][CH:3]([CH3:5])[CH3:4])=[C:9]([N+:19]([O-:21])=[O:20])[CH:10]=1)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 84680854-fluoro-N-methyl-3-nitrobenzenesulfonamide

Product 1

HCID 699352384-Isopropoxy-N-methyl-3-nitrobenzenesulfonamideYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaH (0.440 g, 11 mmol) was added to 20 mL of isopropanol and the resulting mixture stirred at room temperature. After 30 minutes, 4-fluoro-N-methyl-3-nitrobenzenesulfonamide (2.34 g, 10 mmol) was added. The reaction mixture was then stirred at room temperature overnight. The mixture was poured into EtOAc and water. The organic phase was separated, dried over Na2SO4, and concentrated in vacuo to give the crude product. Purification via column chromatography (1:1 petroleum ether/ethyl acetate) afforded N-methyl-4-[(1-methylethyl)oxy]-3-nitrobenzenesulfonamide (1.6 g, 58% yield) as a yellow solid. MS (m/z) 274.7 (M+H+)

Workup

  1. stirringThe reaction mixture was then stirred at room temperature overnight
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customPurification via column chromatography (1:1 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-16445e4b802040e1b77f22b45efca9d6
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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