Methylamine → 3-cyano-N-methyl-5-nitrobenzenesulfonamide

HRID 889442Notes

Reaction equation

HRID 889442 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:12](Cl)(=[O:14])=[O:13])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1)#[N:2].[CH3:16][NH2:17]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([S:12]([NH:17][CH3:16])(=[O:14])=[O:13])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 55279240HCID 55279240, compound

Product 1

HCID 593137343-cyano-N-methyl-5-nitrobenzenesulfonamideYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Intermediate 71B (150 mg, 0.61 mmol) in DCM (4 mL) was added methylamine (2.0 M solution in THF, 1.5 mL, 3.0 mmol) and TEA (0.424 mL, 3.04 mmol). The reaction mixture was stirred at room temperature for 1 hour, diluted with DCM, washed with water, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (flash chromatography, 12 g, EtOAC/hexane=0-100%) to give Intermediate 71C (45 mg, 31%) as a white solid. HPLC: Rt=1.112 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm). 1H NMR (500 MHz, CDCl3) δ ppm 8.90 (1H, s), 8.71 (1H, s), 8.46 (1H, s), 4.76 (1H, br. s.), 2.81 (3H, d, J=4.95 Hz).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (flash chromatography, 12 g, EtOAC/hexane=0-100%)

Sources & evidence

ORD record
ord-6c3fd811d6f74a619fa4a754031e89e4
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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