Aniline → N-phenyl-3-chloropropylsulfonamide

HRID 36878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 36878
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>N1C=CC=CC=1>[C:10]1([NH:9][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 154103-Chloropropanesulphonyl chloride

Produkt 1

HCID 10014230N-phenyl-3-chloropropylsulfonamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-Chloropropylsulfonyl chloride 1 (1.456 g,8.23 mmol) was added dropwise to a solution of aniline (0.5 ml, 8.23 mmol) in pyridine (5 ml) with cooling at -20° to -30° C. over about 5 minutes. After the completion of the addition, the reaction mixture was stirred for another 45 minutes at room temperature. The reaction mixture was concentrated in vacuo and the residue was subjected to column chromatography on silica gel. From the fraction eluted with a mixture of ethyl acetate/n-hexane (1:2), 1.683 g (88%) of N-phenyl-3-chloropropylsulfonamide (intermediate 3j) was obtained as a yellow oil, which, when treated in a manner similar to that described in Preparation 1, gave the objective compound 4j as a pale yellow solid (yield 57%).

Aufarbeitung

  1. temperaturewith cooling at -20° to -30° C. over about 5 minutes
  2. additionAfter the completion of the addition
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washFrom the fraction eluted with a mixture of ethyl acetate/n-hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-755c19f4d4554402bcc4edcb827978e2
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418230

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