Ethanol → 4-[15-(Trifluoromethyl)pentadecylamino]cinnamic acid

HRID 1659946Notes

Reaction equation

HRID 1659946 reaction equation
[F:1][C:2]([F:33])([F:32])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:31]=[CH:30][C:22]([CH:23]=[CH:24][C:25]([O:27]CC)=[O:26])=[CH:21][CH:20]=1.[OH-].[Na+].O.C(O)C>C(O)(=O)C>[F:1][C:2]([F:32])([F:33])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:31]=[CH:30][C:22]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 54517974Ethyl 4-[15-(trifluoromethyl)pentadecylamino]cinnamate

Product 1

HCID 544131044-[15-(Trifluoromethyl)pentadecylamino]cinnamic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 4-aminocinnamate, one equivalent of 15-(trifluoromethyl)pentadecyl bromide and one equivalent of anhydrous potassium carbonate in hexamethylphosphoramide is heated for 20 hours at 60° C. The mixture is then cooled, diluted with water and extracted with ether. The combined ether extracts are dried, filtered and evaporated to provide ethyl 4-[15-(trifluoromethyl)pentadecylamino]cinnamate. The ester is hydrolyzed with sodium hydroxide in a 1:9 water:ethanol solution at steam bath temperatures for 10 hours. The hot solution is then acidified with acetic acid, cooled and filtered and the solid is washed with water. Recrystallization from chloroform yields the product as a white solid.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washthe solid is washed with water
  4. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-851900059fbd4ecc9ae8e5543d5595ed
Source dataset
uspto-grants-1981_12
Patent number
US04305959

Reaction notes

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