Nitric Acid → HCID 14819589, compound

HRID 1776478Notes

Reaction equation

HRID 1776478 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:3][CH2:2]1.[N+:17]([O-])([OH:19])=[O:18]>CCOC(C)=O>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=[CH:8][C:7]=2[NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 86679430HCID 86679430, compound

Product 1

HCID 14819589HCID 14819589, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(2-(cyclopropylmethoxy)phenyl)methanesulfonamide (1.3 g, 5.39 mmol) was cooled to 0° C., and nitric acid (0.746 ml, 10.77 mmol) was added. The mixture was stirred at RT for 1 hour. The mixture was diluted with EtOAc and washed with NaHCO3 5% and brine. The organic phase was dried over Na2SO4, and the solvent was removed. The crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=80:20 to 60:40). 0.390 g of title product were obtained by collection and evaporation of clean fractions. Product obtained from mixed fractions was triturated with EtOAc affording 0.285 g of title compound. The mother liquor from trituration was evaporated and purified by flash chromatography on silica gel (DCM:petroleum ether=80:20) to give 0.155 g of title compound. Title product N-(2-(cyclopropylmethoxy)-4-nitrophenyl)-methanesulfonamide was obtained (0.830 g, 2.90 mmol, 53.8% yield, MS/ESI+ 286.9 [MH]+).

Workup

  1. washwashed with NaHCO3 5% and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed
  4. customThe crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=80:20 to 60:40)

Sources & evidence

ORD record
ord-706ae27ec164412b9969f2d44e0cabfa
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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