Stearoyl chloride → HCID 21832995, compound

HRID 1740767Notes

Reaction equation

HRID 1740767 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:12]=[C:13]([NH2:20])[C:14](=[CH:18][CH:19]=1)[C:15]([OH:17])=[O:16])([O-:10])=[O:9].[C:21](Cl)(=O)[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][CH2:37][CH3:38].C(Cl)(=O)OCC>C(Cl)Cl>[CH2:37]([C:38]1[O:16][C:15](=[O:17])[C:14]2[CH:18]=[CH:19][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][C:13]=2[N:20]=1)[CH2:36][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][CH3:21]

Participants

6

Reactant 4

HCID 8212Stearoyl chlorideHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 120764-Nitroanthranilic acid

Product 1

HCID 21832995HCID 21832995, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (4.85 ml) was added to a suspension of 4-nitroanthranilic acid (3.00 g) in methylene chloride (30 ml) and then the mixture was cooled with ice. The reaction mixture, with stearoyl chloride (4.99 g) dropwise added thereto, was stirred for 3.25 hours at room temperature and then was cooled with ice. Then, triethylamine (2.55 ml) and ethyl chlorocarbonate (1.74 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 200 g, chloroform-hexane), thereby yielding 3.62 g of the aimed compound as colorless solid.

Workup

  1. temperaturethe mixture was cooled with ice
  2. temperaturewas cooled 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 200 g, chloroform-hexane)

Sources & evidence

ORD record
ord-9be4fdb95e2c4c3284677109d99d02d5
Source dataset
uspto-grants-1999_10
Patent number
US05972929

Reaction notes

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