Palmitoyl chloride → Ethyl 3-fluoro-4-(hexadecanoylamino)benzoate

HRID 1156105Notes

Reaction equation

HRID 1156105 reaction equation
[C:1](Cl)(=[O:17])[CH2:2][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][CH3:16].[NH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][C:21]=1[F:31]>C(Cl)Cl>[F:31][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][C:20]=1[NH:19][C:1](=[O:17])[CH2:2][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][CH3:16])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 20536493Ethyl 4-Amino-3-fluorobenzoate

Product 1

HCID 20536492Ethyl 3-fluoro-4-(hexadecanoylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of hexadecanoyl chloride (20 g) in 100 ml of methylene chloride is slowly added with stirring to a solution of 20 g of ethyl 4-amino-3-fluorobenzoate in 100 ml of methylene chloride. The mixture is filtered and the filtrate is washed with dilute hydrochloric acid and water, dried and the solvent evaporated. Crystallization of the residue from acetonitrile affords ethyl 3-fluoro-4-(hexadecanoylamino)benzoate.

Workup

  1. filtrationThe mixture is filtered
  2. washthe filtrate is washed with dilute hydrochloric acid and water
  3. customdried
  4. customthe solvent evaporated
  5. customCrystallization of the residue from acetonitrile

Sources & evidence

ORD record
ord-bf29e2917c8a4844beaabe6d3283011f
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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