Dimethylamine → HCID 9834935, Verbindung

HRID 1167241

Reaktionsgleichung

Reaktionsgleichung von HRID 1167241
[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]

Komponenten

7

Edukt 3

HCID 674DimethylamineHCID 69914-Nitro-m-xyleneHCID 24638Chlorosulfonic acid

Produkt 1

HCID 9834935HCID 9834935, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-cfcef51d76e14bb9b49ffe780ca6a967
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617357B2

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