1-Bromohexadecane → Ethyl 4-hexadecylaminocinnamate

HRID 1156142Notes

Reaction equation

HRID 1156142 reaction equation
F[C:2]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:3]=1[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)P(N(C)C)(N(C)C)=O.O>[CH2:32]([NH:15][C:13]1[CH:12]=[CH:11][C:3]([CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:2][CH:14]=1)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]

Participants

6

Reactant 3

HCID 82131-BromohexadecaneHCID 11430Potassium CarbonateHCID 53987187Ethyl 3-(4-amino-2-fluorophenyl)prop-2-enoate

Product 1

HCID 53709874Ethyl 4-hexadecylaminocinnamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-fluoro-4-aminocinnamate, one equivalent of 1-bromohexadecane 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-hexadecylaminocinnamate. 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 2-fluoro-4-(hexadecylamino)cinnamic acid.

Workup

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

Sources & evidence

ORD record
ord-03c5fbe2059e4c70b4006d3fb7efee4f
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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