Stearoyl chloride → HCID 21833011, compound

HRID 1740766Notes

Reaction equation

HRID 1740766 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].[C:20](Cl)(=O)[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][CH2:34][CH2:35][CH2:36][CH3:37].C(Cl)(=O)OCC>C(Cl)Cl>[CH2:36]([C:37]1[O:12][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[C:17]([O:18][CH3:19])[C:9]=2[N:8]=1)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20]

Participants

6

Reactant 4

HCID 8212Stearoyl chlorideHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 21833011HCID 21833011, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (5.30 ml) was added to a suspension of 2-amino-3-methoxybenzoic acid (3.00 g) in methylene chloride (30 ml). The mixture was cooled with ice and stearoyl chloride (5.44 g) was dropwise added thereto. The reaction mixture was stirred for 2.5 hours at room temperature and then cooled with ice. Then, triethylamine (2.80 ml) and ethyl chlorocarbonate (1.88 ml) were added to the reaction mixture successively. The reaction mixture was stirred for 1 hour at 0° C. and for 3 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 150 g, chloroform-hexane), thereby yielding 3.73 g of the aimed compound as colorless solid.

Workup

  1. additionwas dropwise added
  2. temperaturecooled with ice
  3. stirringThe reaction mixture was stirred for 1 hour at 0° C. and for 3 hours at room temperature successively
  4. concentrationconcentrated
  5. additionThe residue, with chloroform added
  6. washwas washed with water and saturated brine successively
  7. dry with materialThe organic layer was dried over sodium sulfate anhydride
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (silica gel 150 g, chloroform-hexane)

Sources & evidence

ORD record
ord-69d63fef178f4f0a812caa6b4567d3d6
Source dataset
uspto-grants-1999_10
Patent number
US05972929

Reaction notes

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