Benzenesulfonamide, 3-nitro-N-phenyl- → Benzenesulfonamide, 3-amino-N-phenyl-

HRID 1803918Notes

Reaction equation

HRID 1803918 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C1COCC1.CCOC(C)=O>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 120051Benzenesulfonamide, 3-nitro-N-phenyl-

Product 1

HCID 66454Benzenesulfonamide, 3-amino-N-phenyl-Yield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

To 3-nitro-N-phenylbenzenesulfonamide (255.5 mg, 0.919 mmol) in 4 mL of THF is added SnCl2 dihydrate (1.015 g, 4.486 mmol). The resulting mixture is heated in a microwave reactor at a power of 75 Watts and 135° C. for 1 min then at 15 Watts and 135° C. for 14 min. The reaction is cooled to room temperature, diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3 (10 mL) and allowed to stir for about 12 hours. The reaction mixture is then extracted with EtOAc (75 mL). The organic layer is washed with H2O (75 mL), saturated aqueous NaCl (2×75 mL), dried (MgSO4) and concentrated in vacuo to yield a yellow residue. This residue is purified over silica (0-4% MeOH in CH2Cl2) to afford 178 mg (78% yield) of the desired compound. 1H NMR (DMSO-d6, 300 MHz): δ 5.57 (s, 2H), 6.69 (d, J=8.1 Hz, 1H), 6.84 (d, J=7.5 Hz, 1H), 6.95 (s, 1H), 6.99 (t, J=7.5 Hz, 1H), 7.07 (d, J=8.1 Hz, 2H), 7.12 (t, J=8.1 Hz, 1H), 7.21 (t, J=8.1 Hz, 2H), 10.12 (s, 1H). MS (ESI, pos. ion) m/z: 249 (M+1).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. washwashed with saturated aqueous NaHCO3 (10 mL)
  3. extractionThe reaction mixture is then extracted with EtOAc (75 mL)
  4. washThe organic layer is washed with H2O (75 mL), saturated aqueous NaCl (2×75 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a yellow residue
  8. customThis residue is purified over silica (0-4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-79c047f6b9b946d9a59a1ad6099fe47b
Source dataset
uspto-grants-2013_01
Patent number
US08354407B2

Reaction notes

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