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

HRID 2198488

반응식

HRID 2198488 반응식
O.Cl.[F:3][C:4]([F:26])([F:25])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[C:10]2[NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1.CN(C)C=O.[CH2:32]([N:34]([CH2:40][CH3:41])[CH2:35][CH2:36][NH:37][CH2:38][CH3:39])[CH3:33].C(=O)([O-])[O-].[Na+].[Na+]>S(Cl)(Cl)=O.C(Cl)(Cl)Cl.O.CCOCC>[CH2:32]([N:34]([CH2:40][CH3:41])[CH2:35][CH2:36][N:37]([CH2:38][CH3:39])[C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:10]2[C:9]3[C:14](=[C:5]([C:4]([F:25])([F:3])[F:26])[CH:6]=[CH:7][CH:8]=3)[N:13]=[CH:12][CH:11]=2)=[CH:24][CH:23]=1)[CH3:33]

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 66040TriethylethylenediamineHCID 705455024-(8-Trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride monohydrate

생성물 1

HCID 20520149N-(2-diethylaminoethyl)-N-ethyl-4-(8-trifluoromethyl-4-quinolylamino)benzamide수율 64%

시약·촉매·용매 4

HCID 24386Thionyl Chloride촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6212Chloroform용매

실험 절차

11.6 Grams (0.03 mole) of 4-(8-trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride monohydrate were refluxed in 80 milliliters of thionyl chloride containing two drops of dimethyl formamide for 11/2 hours. 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'-triethyl ethylenediamine 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 a gummy solid, which was largely taken up in ether. On concentration of this solution a colourless solid crystallised out, which was collected to give 8.8 grams (63% yield) of N-(2-diethylaminoethyl)-N-ethyl-4-(8-trifluoromethyl-4-quinolylamino)benzamide quarter hydrate, m.p. 151°-152° C.

후처리

  1. customThe thionyl chloride was evaporated off
  2. addition50 milliliters of benzene were added
  3. customevaporated
  4. additionThe resulting acid chloride hydrochloride was added in portions
  5. waitto stand overnight
  6. customThe chloroform layer was separated
  7. customdried
  8. customthe chloroform evaporated
  9. customto give a gummy solid, which
  10. customOn concentration of this solution a colourless solid crystallised out
  11. customwhich was collected

출처 및 근거

ORD 기록
ord-040fa951ae274dd09b72d85c9cc46476
출처 데이터셋
uspto-grants-1982_11
특허 번호
US04357333

연결된 노트

불러오는 중…