HCID 47464241, compound → HCID 61024364, compound

HRID 536042Notes

Reaction equation

HRID 536042 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[C:8]([N+:14]([O-])=O)[CH:7]=1)(=[O:5])=[O:4]>C(O)C.[NH4+].[Cl-].[Zn]>[NH2:14][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][CH3:13]

Participants

5

Reactant 1

HCID 47464241HCID 47464241, compound

Product 1

HCID 61024364HCID 61024364, compoundYield 56.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of N-methyl-4-(methylthio)-3-nitrobenzenesulfonamide (1.0 g, 3.81 mmol) in 10 mL of ethanol and 10 mL of NH4Cl, zinc dust (2.5 g, 3.81 mmol) was added. The reaction mixture was stirred overnight at room temperature. The mixture was then filtered and diluted with ethyl acetate and water. The organic phase was separated, washed with water and brine, dried over MgSO4, filtered and concentrated to afford 3-amino-N-methyl-4-(methylthio)benzenesulfonamide (0.500 g, 56%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.06 (d, J=8.03 Hz, 1H), 6.86 (s, 1H), 6.67-6.76 (m, 1H), 5.28 (br. s., 2H), 2.17 (s, 3H), 2.21 (s, 3H); MS (m/z) 232.7 (M+H+)

Workup

  1. filtrationThe mixture was then filtered
  2. additiondiluted with ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5483e72075ff4caaabef63127a9f9e49
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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