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

HRID 2268266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268266
[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-dimethylethy] 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-facdcf5c2b0f4699ad304b55f03ace57
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326500B1

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