반응 #2285670

반응 방정식

N,N,N'-triethyl ethylenediamine

sodium carbonate

4-(8-trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride monohydrate

dimethyl formamide

→

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

수율 64.0%

용매

ether

chloroform

water

반응 조건

후처리

1. 1
   기타The thionyl chloride was evaporated off
2. 2
   workup.ADDITION50 milliliters of benzene were added
3. 3
   기타evaporated
4. 4
   workup.ADDITIONThe resulting acid chloride hydrochloride was added in portions
5. 5
   workup.WAITto stand overnight
6. 6
   기타The chloroform layer was separated
7. 7
   기타dried
8. 8
   기타the chloroform evaporated
9. 9
   기타to give a gummy solid, which
10. 10
    기타On concentration of this solution a colourless solid crystallised out
11. 11
    기타which was collected

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.

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