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

HRID 2198488

Reaction equation

HRID 2198488 reaction equation
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]

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 24386Thionyl ChlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-040fa951ae274dd09b72d85c9cc46476
Source dataset
uspto-grants-1982_11
Patent number
US04357333

Linked notes

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