Nitric Acid → HCID 45076974, compound

HRID 507350Notes

Reaction equation

HRID 507350 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[N+:12]([C:10]1[C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=[CH:8][C:9]=1[CH3:11])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 76253Benzothiazole, 2,6-dimethyl-

Product 1

HCID 45076974HCID 45076974, compoundYield 256.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-dimethylbenzothiazol (350 mg, 2.15 mmol) in Conc. H2SO4 (4 mL) was added HNO3 (69%, 0.3 mmol) at 0° C. After stirred at 0° C. for 0.5 h, the mixture was poured over ice-water. The precipitate was collected and washed with 5% sodium bicarbonate and water, recrystallized from ethanol to give 7-nitro-2,6-dimethylbenzothiazol as yellow solid (160 mg). The product (150 mg) was hydrogenated over 5% Pd/C in ethanol-THF (10:2 mL) at atmosphere pressure to give 2,6-dimethyl-benzothiazol-7-ylamine as yellow solid (120 mg). TLC single spot at Rf 0.55 (10% EtOAc/DCM); 1H NMR (270 MHz, DMSO): δ 7.07 (2H, s, ArH), 5.23 (2H, s, NH2), 2.73 (3H, s, CH3), 2.20 (3H, s, CH3).

Workup

  1. customThe precipitate was collected
  2. washwashed with 5% sodium bicarbonate and water
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3ed877ba1e8548078565959871cdf495
Source dataset
uspto-grants-2010_08
Patent number
US07786152B2

Reaction notes

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