Stannous chloride dihydrate → 2-(2-Amino-4-chlorophenylsulfanyl)-benzoic acid methyl ester

HRID 2109902Notes

Reaction equation

HRID 2109902 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[N+:18]([O-])=O.O.O.Cl[Sn]Cl>CCO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[NH2:18]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 16762830Methyl 2-[(4-chloro-2-nitrophenyl)thio]benzoate

Product 1

HCID 186908772-(2-Amino-4-chlorophenylsulfanyl)-benzoic acid methyl esterYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-(4-chloro-2-nitro-phenylsulfanyl)-benzoic acid methyl ester (189JO09) (232 mg, 0.72 mmol) in EtOH (5 mL) was added SnCl2.2H2O (812 mg, 3.6 mmol) and the resulting mixture was stirred at 80° C. for 2 h and then concentrated. The residue was treated with ice, and then Na2CO3 was added until a pH of 10 was reached. EtOAc was added and the slurry was filtered through celite. The EtOAc-phase was washed with water and brine, dried (Na2SO4) and concentrated to give 149 mg (70%) of the title compound (189JO11). 1H NMR (CDCl3) δ 8.02 (dd, 1 H, J=1.6, 7.8 Hz), 7.39 (d, 1 H, J=8:2 Hz), 7.29 (m, 1 H), 7.15 (dt, 1 H, J=1.2, 7.8 Hz), 6.87 (d, 1 H, J=2.2 Hz), 6.80 (dd, 1 H, J=2.2, 8.2 Hz), 6.76 (dd, 1 H, J=1.2, 8.0 Hz), 3.96 (s, 3 H).

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with ice
  3. additionNa2CO3 was added until a pH of 10
  4. additionEtOAc was added
  5. filtrationthe slurry was filtered through celite
  6. washThe EtOAc-phase was washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e21932bbcfd04c5f91a07d09f9a258bc
Source dataset
uspto-grants-2009_04
Patent number
US07517871B2

Reaction notes

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