Potassium Carbonate → Ethyl 4-[13-(4-chlorophenyl)tridecylamino]-cinnamate

HRID 2057656Notes

Reaction equation

HRID 2057656 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 97826Ethyl 3-(4-aminophenyl)acrylateHCID 2033130013-(4-Chlorophenyl)tridecyl bromide

Product 1

HCID 53772251Ethyl 4-[13-(4-chlorophenyl)tridecylamino]-cinnamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl p-aminocinnamate, 5.9 g. 13-(4-chlorophenyl)tridecyl bromide and one equivalent of anhydrous powdered potassium carbonate in 50 ml. 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. Crystallization from acetonitrile provides the title compound as white crystals.

Workup

  1. temperatureThe mixture is then cooled
  2. extractionextracted with ether
  3. dry with materialThe combined ether extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-3187173c938e4287a71456aa3716b4c5
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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