HCID 67168207, compound → HCID 67169234, compound

HRID 536060Notes

Reaction equation

HRID 536060 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:8]([N+:16]([O-])=O)[CH:7]=1)(=[O:5])=[O:4]>CCO.[NH4+].[Cl-].[Zn]>[NH2:16][C:8]1[CH:7]=[C:6]([S:3]([NH:2][CH3:1])(=[O:4])=[O:5])[CH:11]=[CH:10][C:9]=1[S:12]([CH3:15])(=[O:13])=[O:14]

Participants

5

Reactant 1

HCID 67168207HCID 67168207, compound

Product 1

HCID 67169234HCID 67169234, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N-methyl-4-(methylsulfonyl)-3-nitrobenzenesulfonamide (1.5 g, crude) in EtOH (20 mL) and saturated aqueous NH4Cl (20 mL) was treated with Zn dust (3.3. g, 51 mmol) and stirred at 50° C. overnight before being filtered (EtOAc wash). The filtrate was diluted with water and extracted with EtOAc. The organic extract was washed with water and brine, dried (MgSO4), concentrated, and subjected to flash chromatography (33% EtOAc-petroleum ether) to give 3-amino-N-methyl-4-(methylsulfonyl)benzenesulfonamide (950 mg, 94% 2 steps) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73 (d, J=8.28 Hz, 1 H), 7.58 (q, J=4.94 Hz, 1 H), 7.34 (d, J=1.76 Hz, 1 H), 7.01 (dd, J=8.53, 1.76 Hz, 1 H), 6.48 (s, 2 H), 3.18 (s, 3 H), 2.47 (d, J=5.02 Hz, 3 H). MS (m/z) 265.0 (M+H+).

Workup

  1. filtrationbefore being filtered
  2. wash(EtOAc wash)
  3. additionThe filtrate was diluted with water
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b6df603863fa477686855a910d8ad277
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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