Cyclohexylamine → N-Cyclohexyl-2-nitrobenzene-1-sulfonamide

HRID 1487233Notes

Reaction equation

HRID 1487233 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].C(N(CC)CC)C.[CH:21]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>ClCCl>[CH:21]1([NH:27][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 818656N-Cyclohexyl-2-nitrobenzene-1-sulfonamideYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-nitrobenzene-1-sulfonyl chloride (22.1 g, 100 mol) in dichloromethane (500 mL) at 0° C. was added triethylamine (14 g, 138.6 mol) and cyclohexanamine (11.9 g, 120.2 mmol) in several portions over 10-15 minutes. The reaction mixture was stirred at room temperature for 4 hours, concentrated and purified by silica gel chromatography to afford the product N-cyclohexyl-2-nitrobenzenesulfonamide (25.7 g, yield 90.5%). 1H NMR (400 MHz, CDCl3) δ ppm 8.16-8.19 (m, 1H), 7.85-7.87 (m, 1H), 7.72-7.78 (m, 2H), 5.24-5.26 (d, 1H, J=7.6 Hz), 3.34-3.36 (m, 1H), 1.77-1.81 (m, 2H), 1.63-1.69 (m, 2H), 1.52-1.56 (m, 1H), 1.17-1.30 (m, 5H).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ca3be115731e41fa8474450e346cfe77
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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