Stearoyl chloride → HCID 15518372, compound

HRID 1532653Notes

Reaction equation

HRID 1532653 reaction equation
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]2[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1.[C:25](Cl)(=O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>C(Cl)(Cl)Cl>[CH2:41]([C:42]1[N:17]([CH2:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][O:8][CH2:13][CH2:12]2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:24]=1)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25]

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 22013772HCID 22013772, compound

Product 1

HCID 15518372HCID 15518372, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

Triethylamine (0.42 ml) was added to a solution containing N-(3-morpholinopropyl)-1,2-benzenediamine (0.640 g) in chloroform (3.5 ml), and then a solution containing stearoyl chloride (0.825 g) in chloroform (3.5 ml) was added thereto while being cooled with ice. After being stirred for 3 hours at room temperature, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (2.25 ml) was added to a solution containing the residue (1.442 g) in ethanol (15 ml). After being stirred for 1.5 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (1.296 g) was purified by silica gel column chromatography (silica gel 40 g, ethyl acetate), thereby yielding the entitled compound (1.088 g) as yellow solid.

Workup

  1. additionwas added
  2. temperaturewhile being cooled with ice
  3. washwashed with saturated sodium hydrogencarbonate aqueous solution and water successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated
  6. additionConcentrated hydrochloric acid (2.25 ml) was added to a solution
  7. additioncontaining the residue (1.442 g) in ethanol (15 ml)
  8. stirringAfter being stirred for 1.5 hours at 90° C.
  9. concentrationthe reaction mixture was concentrated
  10. additionThe residue, with ethyl acetate added
  11. washwas washed with 1N sodium hydroxide aqueous solution and saturated brine successively
  12. dry with materialdried over sodium sulfate anhydride
  13. concentrationconcentrated
  14. customThe residue (1.296 g) was purified by silica gel column chromatography (silica gel 40 g, ethyl acetate)

Sources & evidence

ORD record
ord-41a2988dd10f4466b3b8c94a71790ff5
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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