Nitric Acid → HCID 22125091, compound

HRID 1858321Notes

Reaction equation

HRID 1858321 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12][C:13](=[O:15])[CH3:14])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:12][C:13](=[O:15])[CH3:14])([CH3:11])[CH3:10])=[CH:6][C:7]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 22124971HCID 22124971, compound

Product 1

HCID 22125091HCID 22125091, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

An ice-cooled solution of 3.3 g (12 mmol) of N-[2-(4-bromophenyl)-1,1-dimethylethyl]-acetamide in 3 ml of concentrated sulfuric acid was treated dropwise with a mixture of 3 ml of concentrated sulfuric acid and 6 ml of 90% nitric acid. After 1 hour the mixture was cautiously added to 200 ml of ice/water and the precipitated product extracted with 150 ml of dichloromethane. The organic solution was dried over magnesium sulfate, filtered and evaporated to give 3.7 g (98%) of N-[2-(4-bromo-3-nitrophenyl)-1,1-dimethyl-ethyl]acetamide as a white solid. [Mass spectrum (ESI) MH+ =315].

Workup

  1. extractionthe precipitated product extracted with 150 ml of dichloromethane
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6bc287991fc74edd96cdd872060cb122
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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