Nitric Acid → 6-Nitro-2-phenylbenzothiazole

HRID 2243078Notes

Reaction equation

HRID 2243078 reaction equation
[C:1]1([C:7]2[S:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:16]([O-])([OH:18])=[O:17]>O>[C:1]1([C:7]2[S:8][C:9]3[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 134392-Phenylbenzothiazole

Product 1

HCID 15126576-Nitro-2-phenylbenzothiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

2-Phenylbenzothiazole (Aldrich, 63.89 g, 0.302 mol) is nitrated with 100% nitric acid (190 ml, 4.53 mol) at 5° C. The mixture is stirred at 5° C. for 70 minutes, quenched in ice-water and basified with 32% NaOH (pH=10). The product is filtered off and the solid obtained is suspended in water and filtered off. The product is recrystallized from isopropyl ether. Yield: 73.6 g (95%); Rf (8/2 petroleum ether/ethyl acetate): 0.76; m.p.: 178.9-181.3°; 1H-NMR (d6-DMSO): 9.16 (d, 1H); 8.35 (dd, 1H); 8.23 (d, 1H); 8.15 (dd, 1H) 7.58; (m, 4H).

Workup

  1. customquenched in ice-water
  2. filtrationThe product is filtered off
  3. customthe solid obtained
  4. filtrationfiltered off
  5. customThe product is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-4a181e5ddeaa45a99cc2bafa94475fbe
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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