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Sodium Carbonate → N-(2-diethylaminoethyl)-N-ethyl-2-(8-trifluoromethyl-4-quinolylamino)benzamide

HRID 2198485
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HRID 2198485 반응식
O.O.Cl.[F:4][C:5]([F:27])([F:26])[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[C:11]2[NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=O.[CH2:28]([N:30]([CH2:36][CH3:37])[CH2:31][CH2:32][NH:33][CH2:34][CH3:35])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>S(Cl)(Cl)=O.C(Cl)(Cl)Cl.O.CCOCC>[CH2:28]([N:30]([CH2:36][CH3:37])[CH2:31][CH2:32][N:33]([CH2:34][CH3:35])[C:19](=[O:21])[C:18]1[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=1[NH:16][C:11]1[C:10]2[C:15](=[C:6]([C:5]([F:26])([F:4])[F:27])[CH:7]=[CH:8][CH:9]=2)[N:14]=[CH:13][CH:12]=1)[CH3:29]
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참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 66040TriethylethylenediamineHCID 705463792-(8-Trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride dihydrate

생성물 1

HCID 20520140N-(2-diethylaminoethyl)-N-ethyl-2-(8-trifluoromethyl-4-quinolylamino)benzamide수율 46.2%

시약·촉매·용매 4

HCID 962Water용매
HCID 3283
Diethyl Ether
용매
HCID 6212Chloroform용매
HCID 24386Thionyl Chloride용매

실험 절차

12.1 Grams (0.03 mole) of 2-(8-trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride dihydrate were refluxed in 80 milliliters of thionyl chloride for half an hour. A yellow solid precipitated. The thionyl chloride was evaporated off and 50 milliliters of benzene were added and evaporated. The resulting acid chloride hydrochloride was added in portions with stirring to a cooled mixture of 4.32 grams (0.03 mole) of N,N,N'-triethylethylenediamine in 80 milliliters of chloroform and 31.8 grams (0.3 mole) of sodium carbonate in 100 milliliters of water. The mixture was stirred for one hour, and allowed to stand overnight. The chloroform layer was separated and dried and the chloroform evaporated to give an oil, which could not be solidified. The oil was dissolved in ether and purified by chromatography on an alumina (type H) column. Elution with ether/chloroform (50:50) gave a pale yellow oil which was kept under vacuum for four days when it gradually solidified to give 6.35 grams (46% yield) of title compound of melting point 112°-113° C.

후처리

  1. customA yellow solid precipitated
  2. customThe thionyl chloride was evaporated off
  3. addition50 milliliters of benzene were added
  4. customevaporated
  5. additionThe resulting acid chloride hydrochloride was added in portions
  6. waitto stand overnight
  7. customThe chloroform layer was separated
  8. customdried
  9. customthe chloroform evaporated
  10. customto give an oil, which could not
  11. custompurified by chromatography on an alumina (type H) column
  12. washElution with ether/chloroform (50:50)
  13. customgave a pale yellow oil which
  14. waitwas kept under vacuum for four days

출처 및 근거

ORD 기록
ord-dd65826eaac2415690c96a7254070999
출처 데이터셋
uspto-grants-1982_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04357333

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