Water → 2-chloro-N-(4-chlorobutyl-sulphonyl)-4-methyl-aniline

HRID 2094298

Reaktionsgleichung

Reaktionsgleichung von HRID 2094298
[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15](Cl)(=[O:17])=[O:16].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH:4][S:15]([CH2:14][CH2:13][CH2:12][CH2:11][Cl:10])(=[O:17])=[O:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 120072-Chloro-p-toluidineHCID 742124-Chlorobutane-1-sulphonyl chloride

Produkt 1

HCID 670486822-chloro-N-(4-chlorobutyl-sulphonyl)-4-methyl-aniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1.30 ml (10.7 mmol) 2-chloro-4-methyl-aniline are placed in 30 ml of pyridine, combined with 2.67 g (10.5 mmol) 75% m 4-chlorobutyl-sulphonic acid chloride and stirred for 16 hours at ambient temperature. The reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with 6-molar hydrochloric acid, dried over sodium sulphate and evaporated down i. vac. The residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=9:1->7:3).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed with 6-molar hydrochloric acid
  3. dry with materialdried over sodium sulphate
  4. customevaporated down i
  5. customThe residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=9:1->7:3)

Quellen und Nachweise

ORD-Eintrag
ord-957bc4cd6cfb40abb579adba44d52d11
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445525B2

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