Anthranilic Acid → HCID 11710756, compound

HRID 1740763Notes

Reaction equation

HRID 1740763 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](O)(=[O:42])[C:35]1[C:36](=[CH:38][CH:39]=[CH:40][CH:41]=1)[NH2:37]>C(Cl)Cl>[CH2:9]([C:8]1[O:27][C:34](=[O:42])[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=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][CH3:25]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 5281Stearic AcidHCID 8471Triethylamine3×HCID 10928Ethyl chloroformate2×

Product 1

HCID 11710756HCID 11710756, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 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 mixed 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 45C and cooled with ice. The reaction mixture, with triethylamine (0.46 ml) and ethyl chlorocarbonate (0.32 ml) dropwise added thereto, was stirred for 1 hour at 0° C. and for 1.5 hours at room temperature successively, and then concentrated. The residue, with ethyl acetate added thereto, was washed with water, neutralized with diluted hydrochloric acid, and washed with saturated brine. The organic layer was dried over magnesium sulfate anhydride and then concentrated. The residue was purified by silica gel column chromatography (silica gel 35 g, chloroform-methanol), thereby yielding 966 mg of the aimed compound as colorless crystals.

Workup

  1. temperaturewhile being cooled with ice
  2. temperaturecooled with ice
  3. stirringwas stirred for 1 hour at 0° C. and for 1.5 hours at room temperature successively
  4. concentrationconcentrated
  5. additionThe residue, with ethyl acetate added
  6. washwas washed with water
  7. washwashed with saturated brine
  8. dry with materialThe organic layer was dried over magnesium sulfate anhydride
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (silica gel 35 g, chloroform-methanol)

Sources & evidence

ORD record
ord-638bf13ab626499fae345022fb26138c
Source dataset
uspto-grants-1999_10
Patent number
US05972929

Reaction notes

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