Hydrochloric Acid → 2-[4-(2-Phenyl-thiazol-4-yl)-phenyl]-ethylamine

HRID 413295

Reaktionsgleichung

Reaktionsgleichung von HRID 413295
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH:20]C(=O)C)=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][NH2:20])=[CH:16][CH:17]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9343045N-[2-[4-(2-Phenyl-thiazol-4-yl)-phenyl]-ethyl}-acetamide

Produkt 1

HCID 185236422-[4-(2-Phenyl-thiazol-4-yl)-phenyl]-ethylamineAusbeute 85 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a round-bottomed flask, N-{2-[4-(2-phenyl-thiazol-4-yl)-phenyl]-ethyl}-acetamide (838 mg, 2.60 mmol) was added to 5.0 ml of concentrated HCl and the resulting solution was heated to about 120° C. for about sixteen hours. The solution was then cooled to about 0° C., brought to pH 12 with 5M sodium hydroxide, and extracted with four portions of methylene chloride. The combined organic extracts were then washed with brine, dried over magnesium sulfate, and concentrated in vacua. The crude material was purified by column chromatography (silica gel; methylene chloride to 20% methanol/methylene chloride) to afford the product (617 mg, 85% yield). LRMS ([M+H]+)=281.2.

Aufarbeitung

  1. temperatureThe solution was then cooled to about 0° C.
  2. extractionextracted with four portions of methylene chloride
  3. washThe combined organic extracts were then washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacua
  6. customThe crude material was purified by column chromatography (silica gel; methylene chloride to 20% methanol/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-5cdb3a85fe5b43e49e389d3914f454b2
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566377B2

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