N-cyclohexyl-2-nitrobenzenesulfonamide → 2-Amino-N-cyclohexylbenzene-1-sulfonamide

HRID 1487234Notes

Reaction equation

HRID 1487234 reaction equation
[CH:1]1([NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[NH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:8]([NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:10])=[O:9]

Participants

4

Reactant 1

HCID 818656N-cyclohexyl-2-nitrobenzenesulfonamide

Product 1

HCID 11328342-Amino-N-cyclohexylbenzene-1-sulfonamideYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-cyclohexyl-2-nitrobenzenesulfonamide (25.7 g, 90.5 mmol) in methanol (500 mL) was added palladium on carbon (10%). The mixture was stirred under an atmosphere of hydrogen for 12 hours. The catalyst was removed by filtration and the filtrate was evaporated to afford the product 2-amino-N-cyclohexylbenzenesulfonamide (22 g, yield 95.7%). 1H NMR (400 MHz, CDCl3) δ ppm 7.72-7.74 (dd, 1H, J=1.2 Hz, 8.0 Hz), 7.27-7.33 (m, 1H), 6.75-6.82 (m, 2H), 4.84 (s, 3H), 3.05-3.07 (m, 1H), 1.59-1.70 (m, 4H), 1.46-1.50 (m, 1H), 1.08-1.22 (m, 5H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-08aad39cf78844f9b3a6191662b1e831
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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