Stannous chloride dihydrate → 2-(4'-Aminophenyl)-6-methylsulfoxy benzothiazole

HRID 1797775Notes

Reaction equation

HRID 1797775 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][S:21]([OH:24])(=[O:23])=[O:22])[C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][S:21]([OH:24])(=[O:23])=[O:22])[C:13]=3[N:14]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 672640042-(4'-Nitrophenyl)-6-methylsulfoxy benzothiazole

Product 1

HCID 672640372-(4'-Aminophenyl)-6-methylsulfoxy benzothiazoleYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(4′-nitrophenyl)-6-methylsulfoxy benzothiazole (35 mg, 0.10 mmol) dissolved in ethanol (10 mL) was added SnCl2.2H2O (50 mg). The reaction mixture was heated to reflux for 1.5 hr. The solvent was then removed under reduced pressure. The residue was dissolved in ethyl acetate (10 mL), washed with 1N NaOH, water, dried over MgSO4. Evaporation of the solvent afforded 2-(4′-aminophenyl)-6-methylsulfoxy benzothiazole (21 mg, 65%) as pale brown solid. 1HNMR (300 MHz, CDCl3) δ (ppm): 8.02(d, J=6.2 Hz, 1H), 7.92(d, J=8.7 Hz, 2H), 7.84(d, J=2.4 Hz, 1H), 7.38(dd, J1=2.4 Hz, J2=6.2 Hz, 1H), 6.78(d, J=8.7 Hz, 2H), 2.21(s, 3H, CH3).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 hr
  3. customThe solvent was then removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  5. washwashed with 1N NaOH, water
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-64be9c6243234337a7e70793f4f6778c
Source dataset
uspto-grants-2013_01
Patent number
US08343457B2

Reaction notes

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