Nitric Acid → HCID 22272693, compound

HRID 1064804Notes

Reaction equation

HRID 1064804 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])=[O:4].[N+:18]([O-])([OH:20])=[O:19]>S(=O)(=O)(O)O>[Br:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:13])[CH3:14])=[CH:10][CH:9]=[C:8]([N+:18]([O-:20])=[O:19])[C:7]=1[CH:15]([CH3:17])[CH3:16])=[O:4]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12149064Acetamide, N-[2,6-bis(1-methylethyl)phenyl]-2-bromo-

Product 1

HCID 22272693HCID 22272693, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

2-Bromo-N-(2,6-diisopropylphenyl)acetamide (5.96 g, 20 mmol) was dissolved in concentrated sulfuric acid (100 ml) with ice-cooling, a solution of fuming nitric acid (1.51 g, 24 mmol) dissolved in concentrated sulfuric acid (10 ml) was dropped thereinto and the mixture was stirred for 10 minutes. The reaction solution was poured onto ice water, the separated matters were filtered off and the extraction with ethyl acetate was conducted. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over sodium sulfate and the solvent was evaporated therefrom. The residue was recrystallized from acetone-hexane to provide 6.52 g (yield 95%) of 2-bromo-N-(2,6-diisopropyl-3-nitrophenyl)acetamide as pale yellow needles.

Workup

  1. temperaturecooling
  2. additionwas dropped
  3. additionThe reaction solution was poured onto ice water
  4. filtrationthe separated matters were filtered off
  5. extractionthe extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated sodium chloride solution successively and dried over sodium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-3152c373ba2b49d6bd191e97be7396d5
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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