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

HRID 225129

반응식

HRID 225129 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 233290062-[4-(7-chloro-4-quinolylamino)phenyl]-N-(2-diethylaminoethyl)-N-ethyl acetamide dihydrochloride수율 177.8%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회HCID 3283Diethyl Ether용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-35221640badd499da5c6e3051fb3e7bd
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04235908

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