Dimethylamine → 2,4-dimethyl-5-nitro (N,N-dimethyl)benzenesulfonamide

HRID 1167241

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl[S:13]([OH:16])(=O)=[O:14].[CH3:17][NH:18][CH3:19]>CO.C(Cl)Cl.Cl>[CH3:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][C:5]=1[S:13]([N:18]([CH3:19])[CH3:17])(=[O:16])=[O:14]

Participants

Conditions

Temperature: 130 °C

Procedure

In a dry flask under argon filled with 2,4-dimethyinitrobenzene (1.0 g, 6.61 mmol), chlorosulfonic acid (5 mL) was added dropwise. The resulting solution was stirred at 130° C. for 4 h, and then the mixture was poured slowly onto ice. A light brown precipitate formed and was isolated by filtration. The solid was dissolved in methanol (20 mL), and dimethylamine (3 mL) was added with stirring. After 15 min, the reaction mixture was diluted with methylene chloride and 1 M HCl. The layers were separated, and the organics were dried and concentrated. Purification of the residue by flash chromatography (15% ethyl acetate/hexanes) provided 2,4-dimethyl-5-nitro (N,N-dimethyl)benzenesulfonamide (626 mg, 37%) as a white solid. Anal. Calcd for C10H14N2O4S: C, 46.50; H, 5.46; N, 10.85. Found: C, 46.68; H, 5.25; N, 10.71.

Workup

additionwas added dropwise
additionthe mixture was poured slowly onto ice
customA light brown precipitate formed
customwas isolated by filtration
stirringwith stirring
waitAfter 15 min
customThe layers were separated
customthe organics were dried
concentrationconcentrated
customPurification of the residue by flash chromatography (15% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-cfcef51d76e14bb9b49ffe780ca6a967
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617357B2

Linked notes

Loading…