Anthranilic Acid → 2-(Octadecanoylamino)benzoic acid

HRID 1740762Notes

Reaction equation

HRID 1740762 reaction equation
C(N(CC)CC)C.[C:8]([OH:27])(=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(Cl)(=O)OCC.[C:34]([OH:43])(=[O:42])[C:35]1[C:36](=[CH:38][CH:39]=[CH:40][CH:41]=1)[NH2:37]>C(Cl)Cl.C(Cl)(Cl)Cl>[C:8]([NH:37][C:36]1[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=1[C:34]([OH:43])=[O:42])(=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 5281Stearic AcidHCID 8471Triethylamine2×HCID 10928Ethyl chloroformate

Product 1

HCID 203099812-(Octadecanoylamino)benzoic acidYield 91.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.46 ml) was added to a suspension of stearic acid (853 mg) in methylene chloride (8.5 ml). Then, ethyl chlorocarbonate (0.32 ml) was dropwise added to the mixture while being cooled with ice. After being stirred for 1 hour at 0° C., the mixture, with a solution of anthranilic acid (411 mg) and triethylamine (0.42 ml) in methylene chloride (2 ml) dropwise added thereto, was stirred for 16 hours at 45° C. The reaction mixture was then diluted with chloroform, washed with water and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue was recrystallized from hexane-ethyl acetate mixed solution, thereby yielding 1.107 g of the aimed compound as colorless crystals. According to the comparison by using TLC and 1H-NMR, this product was identified as the aimed compound obtained by Example 1-1 (2).

Workup

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 16 hours at 45° C
  3. washwashed with water and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated
  6. customThe residue was recrystallized from hexane-ethyl acetate mixed solution

Sources & evidence

ORD record
ord-e18dd91ffc4a4870a123fb40092916a1
Source dataset
uspto-grants-1999_10
Patent number
US05972929

Reaction notes

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