3-(Dimethylamino)propyl chloride hydrochloride → {5-[4-(3-Dimethylamino-propoxy)-phenyl]-thiazol-2-yl}phenyl-amine

HRID 1713647

Reaktionsgleichung

Reaktionsgleichung von HRID 1713647
[C:1]1([NH:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26].CC(C)([O-])C.[Na+]>C(O)CCC>[CH3:26][N:25]([CH3:27])[CH2:24][CH2:23][CH2:22][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[S:9][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:12][CH:11]=2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 23676156Sodium t-butoxideHCID 589235364-(2-Phenylamino-thiazol-5-yl)-phenol

Produkt 1

HCID 11245147{5-[4-(3-Dimethylamino-propoxy)-phenyl]-thiazol-2-yl}phenyl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-(2-phenylamino-thiazol-5-yl)-phenol (35 mg, 0.130 mmol), 1-chloro-3-dimethylaminopropane hydrochloride (27 mg, 0.170 mmol, 1.3 equiv), and sodium tert-butoxide (29.6 mg, 0.299 mmol, 2.3 equiv) in 1-butanol (0.2 mL) is heated to 100° C. (using a preheated oil bath) for 3.5 h. The reaction mixture is allowed to cool to RT and concentrated in vacuo. Purification of the crude material by silica gel (10 g) column chromatography (CH2Cl2/MeOH, 90/10→80/20) affords the title compound as a reddish solid: ES-MS: 354.0 [M+H]+; single peak at tR=6.27 min (System 1); Rf=0.09 (CH2Cl2/MeOH, 90/10).

Aufarbeitung

  1. temperatureto cool to RT
  2. concentrationconcentrated in vacuo
  3. customPurification of the crude material by silica gel (10 g) column chromatography (CH2Cl2/MeOH, 90/10→80/20)

Quellen und Nachweise

ORD-Eintrag
ord-4f0ba443b1ea4751a27bc7830cb89a2e
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795288B2

Verknüpfte Notizen

Wird geladen…