Propionic Acid → N-[2-(4-chloro-2,5-xylylthio)-1,1-dimethylethyl]propionamide

HRID 378639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 378639
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([SH:9])=[C:4]([CH3:10])[CH:3]=1.[NH2:11][C:12]([CH3:16])([CH3:15])[CH2:13]O.[C:17](O)(=[O:20])[CH2:18][CH3:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9][CH2:13][C:12]([NH:11][C:17](=[O:20])[CH2:18][CH3:19])([CH3:16])[CH3:15])=[C:4]([CH3:10])[CH:3]=1

Komponenten

5

Edukt 3

HCID 1032Propionic AcidHCID 118072-Amino-2-methyl-1-propanolHCID 1088624-Chloro-2,5-dimethylbenzenethiol

Produkt 1

HCID 22007459N-[2-(4-chloro-2,5-xylylthio)-1,1-dimethylethyl]propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-2,5-dimethylbenzenethiol (17.25 g), 2-amino-2-methylpropanol (8.9 g), propionic acid (7.4 g) and toluene (50 ml) was reacted to give a solid which was recrystallised from petroleum ether, b.p. 60-80° C. to give N-[2-(4-chloro-2,5-xylylthio)-1,1-dimethylethyl] propionamide, m.p. 78-81° C. This product (15.0 g) and concentrated hydrochloric acid (18 ml) were boiled under reflux for 25 hours give an oil which was purified by flash column chromatography on silica using ethyl acetate and then ethyl acetate/methanol (4:1) as the mobile phase to give 2-(4-chloro-2,5-xylylthio)-1,1-dimethylethylamine as an oil.

Aufarbeitung

  1. customwas reacted
  2. customto give a solid which
  3. customwas recrystallised from petroleum ether, b.p. 60-80° C.

Quellen und Nachweise

ORD-Eintrag
ord-4185544a36ce4ab1bff3c99726ced250
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06031109

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