Nitric Acid → 4-Methoxy-1-nitrodibenzo[b,d]thiophene

HRID 749285Notes

Reaction equation

HRID 749285 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[S:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[N+:16]([O-])([OH:18])=[O:17].O>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:8]2[S:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([N+:16]([O-:18])=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 4583544-Methoxydibenzothiophene

Product 1

HCID 122571114-Methoxy-1-nitrodibenzo[b,d]thiophene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methoxy-dibenzothiophene (ii)(4.3 g, 20.0 mmol) was dissolved in glacial acetic acid (60 ml) and to this solution was added fuming nitric acid (3.37 ml) in a dropwise fashion ensuring that the temperature of the mixture did not rise above 25° C. The yellow suspension was stirred for a further 45 minutes before being poured carefully into water (200 ml) and stirred for 15 minutes. The yellow solid was removed by filtration and washed thoroughly with copious amounts of water and then hexanes. The residue thus obtained was then dried in a vacuum oven to give the title compound as a yellow solid which was used without any further purification. (5.19 g, 97%) m/z (LC-MS, ESP), RT=4.15 min, (M+H)=260.1

Workup

  1. customdid not rise above 25° C
  2. stirringstirred for 15 minutes
  3. customThe yellow solid was removed by filtration
  4. washwashed thoroughly with copious amounts of water
  5. customThe residue thus obtained
  6. customwas then dried in a vacuum oven

Sources & evidence

ORD record
ord-8ec8526e38714f41ac96069a1cb925be
Source dataset
uspto-grants-2008_07
Patent number
US07402607B2

Reaction notes

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