Nitric Acid → HCID 23085811, compound

HRID 2243080Notes

Reaction equation

HRID 2243080 reaction equation
Cl.[CH2:2]([C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH2:4][CH2:5][CH3:6].FC(F)(F)S(O)(=O)=O.[N+:24]([O-])([OH:26])=[O:25].O>C(Cl)Cl>[CH2:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N+:24]([O-:26])=[O:25])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 23085616HCID 23085616, compound

Product 1

HCID 23085811HCID 23085811, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Pentylbenzothiazole hydrochloride (20.5 g, 0.084 mol) is added, at 0° C., to trifluoromethanesulfonic acid (44.6 ml 0.504 mol) and 100% nitric acid (10.6 ml, 0.215 mol) in methylene chloride (270 ml), and the mixture is stirred at 0° C. for 1.5 hours and at room temperature for one hour. Water (150 ml) is added dropwise and the phases are separated. The organic phase is washed with 0.5M NaHCO3 and with water. The resulting solution is dried, filtered and concentrated. The solid obtained is recrystallized from petroleum ether. Yield: 10.6 g (50%); Rf (8/2 petroleum ether/ethyl acetate): 0.71; 1H-NMR (d6-DMSO) 9.05 (d, 1H); 8.25 (dd, 1H); 8.15 (d, 1H); 3.13 (t, 2H); 1.28-1.36 (m, 4H); 0.85 (t, 3H).

Workup

  1. customthe phases are separated
  2. washThe organic phase is washed with 0.5M NaHCO3 and with water
  3. customThe resulting solution is dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe solid obtained
  7. customis recrystallized from petroleum ether

Sources & evidence

ORD record
ord-f80db7f18fef48fe8e54ab7893f53afe
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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