Palmitoyl chloride → Ethyl 5-hexadecanamido-2-thiophenecarboxylate

HRID 850965Notes

Reaction equation

HRID 850965 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C(Cl)Cl>[C:19]([NH:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1)(=[O:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 21585769Ethyl 5-aminothiophene-2-carboxylate

Product 1

HCID 20503665Ethyl 5-hexadecanamido-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.6 g. of ethyl 5-amino-2-thiophenecarboxylate and 25 ml. of triethylamine in 100 ml. of methylene chloride is added dropwise 16.5 g. of palmitoyl chloride. The reaction mixture is stirred for 20 hours. Evaporation affords an oil. A methylene chloride solution of the oil is filtered and the filtrate passed through Magnesol. Removal of the solvent by evaporation yields a solid which is recrystallized from hexane. A second recrystallization from carbon tetrachloride affords the product.

Workup

  1. customEvaporation
  2. customaffords an oil
  3. filtrationA methylene chloride solution of the oil is filtered
  4. customRemoval of the solvent
  5. customby evaporation
  6. customyields a solid which
  7. customis recrystallized from hexane
  8. customA second recrystallization from carbon tetrachloride
  9. customaffords the product

Sources & evidence

ORD record
ord-00308c91a1db42839f8138bc8b686afc
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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