Hydrochloric Acid → 2-[4-(7-chloro-4-quinolylamino)phenyl]-N-(2-diethylaminoethyl)-N-ethyl acetamide dihydrochloride

HRID 225129

Reaktionsgleichung

Reaktionsgleichung von HRID 225129
[ClH:1].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=O)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[CH2:36]([NH:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH3:37].Cl>CS(C)=O.CCOCC.O>[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([N:38]([CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH2:36][CH3:37])=[O:23])=[CH:18][CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 66040TriethylethylenediamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 705973362-[4-(7-Chloro-4-quinolylamino)phenyl]acetic acid hydrochloride

Produkt 1

HCID 233290062-[4-(7-chloro-4-quinolylamino)phenyl]-N-(2-diethylaminoethyl)-N-ethyl acetamide dihydrochlorideAusbeute 177,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

7.0 Grams (0.02 mole) of 2-[4-(7-chloro-4-quinolylamino)phenyl] acetic acid hydrochloride were dissolved in 150 milliliters of dimethyl sulphoxide by heating the stirred mixture to 50° C. under nitrogen. The solution was cooled to room temperature, 6.48 grams (0.04 mole) of carbonyl diimidazole were added and the mixture was stirred for 21/2 hours under nitrogen. 8.64 Grams (0.06 mole) of triethylethylene diamine was added, the solution was stirred for another 21/2 hrs. and poured into 500 milliliters of water. The mixture was refrigerated overnight and the resulting solid was broken up and stirred with water, but melted at room temperature. The gum was extracted with chloroform and the chloroform layer dried and evaporated to give a yellow oil, which was dissolved in ether. Addition of ethereal HCl gave 9.1 grams (89% yield) of 2-[4-(7-chloro-4-quinolylamino)phenyl]-N-(2-diethylaminoethyl)-N-ethyl acetamide dihydrochloride as a hygroscopic yellow solid, melting point 140°-142° C.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. stirringthe solution was stirred for another 21/2 hrs
  3. waitThe mixture was refrigerated overnight
  4. extractionThe gum was extracted with chloroform
  5. dry with materialthe chloroform layer dried
  6. customevaporated
  7. customto give a yellow oil, which

Quellen und Nachweise

ORD-Eintrag
ord-35221640badd499da5c6e3051fb3e7bd
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04235908

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