Anthranilic Acid → HCID 21833006, compound

HRID 1740765Notes

Reaction equation

HRID 1740765 reaction equation
C(N(CC)CC)C.[C:8]([OH:31])(=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][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(Cl)(=O)OCC.[C:38](O)(=[O:46])[C:39]1[C:40](=[CH:42][CH:43]=[CH:44][CH:45]=1)[NH2:41]>C(Cl)Cl>[CH2:9]([C:8]1[O:31][C:38](=[O:46])[C:39]2[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=2[N:41]=1)[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][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 8215Docosanoic AcidHCID 8471Triethylamine3×HCID 10928Ethyl chloroformate2×

Product 1

HCID 21833006HCID 21833006, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.58 ml) was added to a suspension of behenic acid (3.51 g) in methylene chloride (35 ml). Then, ethyl chlorocarbonate (1.08 ml) was dropwise added to the mixture while being cooled with ice. After being stirred for 1.5 hours at 0° C., the mixture, with a mixed solution of anthranilic acid (1.42 g) and triethylamine (1.44 ml) in methylene chloride (7 ml) dropwise added thereto, was stirred for 3 hour at 0° C. and for 15 hours at room temperature successively, and then cooled with ice. The reaction mixture, with triethylamine (1.58 ml) and ethyl chlorocarbonate (1.08 ml) dropwise added thereto, was stirred for 1 hour at 0° C. and for 2.5 hours at room temperature successively, and then concentrated. The residue, with chloroform added thereto, was washed with water and saturated brine successively. The organic layer was dried over sodium sulfate anhydride, and then concentrated. The residue was purified by silica gel column chromatography (silica gel 100 g, hexane-chloroform), thereby yielding 3.39 g of the aimed compound as colorless solid.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 3 hour at 0° C. and for 15 hours at room temperature successively
  3. temperaturecooled with ice
  4. stirringwas stirred for 1 hour at 0° C. and for 2.5 hours at room temperature successively
  5. concentrationconcentrated
  6. additionThe residue, with chloroform added
  7. washwas washed with water and saturated brine successively
  8. dry with materialThe organic layer was dried over sodium sulfate anhydride
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (silica gel 100 g, hexane-chloroform)

Sources & evidence

ORD record
ord-351a2bc9b2614747a9da4652a8e2231c
Source dataset
uspto-grants-1999_10
Patent number
US05972929

Reaction notes

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