Nitric Acid → 6-Chloro-n-ethyl-3-nitro-2-(trimethylsilyl)benzamide

HRID 356402Notes

Reaction equation

HRID 356402 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].[N+:17]([O-])([OH:19])=[O:18].S(=O)(=O)(O)O>ClCl>[Cl:1][C:2]1[C:3]([C:4]([NH:6][CH2:7][CH3:8])=[O:5])=[C:9]([Si:13]([CH3:15])([CH3:14])[CH3:16])[C:10]([N+:17]([O-:19])=[O:18])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 186303792-Chloro-n-ethyl-6-(trimethylsilyl)benzamide

Product 1

HCID 186302256-Chloro-n-ethyl-3-nitro-2-(trimethylsilyl)benzamideYield 83%

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the amide of example 45 (1.28 g, 5 mmol) in CH2 Cl2 (20 mL) at 0° C. was added dropwise a cold mixture of 70% nitric acid (0.64 mL, 10 mmol) and concentrated sulfuric acid (5 mL) dropwise. The mixture was stirred at 0° C. for 10 min and was poured onto ice. The mixture was extracted with ether, the combined organic layers washed with sat NaHCO3, brine, dried (MgSO4) and concentrated to a solid (1.52 g, 101%). The title compound was obtained by recrystallization from ethyl acetate/hexanes in 83% yield as a white solid. m.p. 147°-149° C.

Workup

  1. additionwas poured onto ice
  2. extractionThe mixture was extracted with ether
  3. washthe combined organic layers washed
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a solid (1.52 g, 101%)

Sources & evidence

ORD record
ord-ffef2d32715c4dbb8cc92a0addc2b9d5
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

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