Pyridine → HCID 53979910, compound

HRID 1952816Notes

Reaction equation

HRID 1952816 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)O[C:9]1[CH:14]=[CH:13][CH:12]=CC=1.[OH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]([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][CH2:42][CH2:43][CH2:44][CH3:45])[CH:26]=[O:27]>C(Cl)(Cl)Cl>[CH2:6]([N:1]([CH2:12][CH2:13][CH2:14][CH3:9])[CH2:2][CH2:19][CH2:20][NH:25][C:26]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]([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][CH2:42][CH2:43][CH2:44][CH3:45])[CH:26]=[O:27])=[O:27])[CH2:5][CH2:4][CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 54074666HCID 54074666, compound

Product 1

HCID 53979910HCID 53979910, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Pyridine (0.67 ml) and phenyl chlorocarbonate (0.76 ml) were added to a suspension of [2-(hydroxymethyl)phenyl]-N-octadecylformamide (2.20 g), which was synthesized in Example 1-1, in chloroform (22 ml) while being cooled with ice. After being stirred for 2 hours at room temperature, the reaction mixture, with chloroform added thereto, was washed with 1N hydrochloric acid, saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated. 3-(Dibutylamino)propylamine (1.36 ml) was added to the residue. After being stirred for 3 hours at 70° C., the reaction mixture was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=60:1-30:1), thereby yielding 3.11 g of the aimed compound as white solid.

Workup

  1. temperaturewhile being cooled with ice
  2. washwas washed with 1N hydrochloric acid, saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated
  5. addition3-(Dibutylamino)propylamine (1.36 ml) was added to the residue
  6. stirringAfter being stirred for 3 hours at 70° C.
  7. customthe reaction mixture was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=60:1-30:1)

Sources & evidence

ORD record
ord-b5c01e25ebe34a8fadd7b4a8292659ab
Source dataset
uspto-grants-2000_09
Patent number
US06114325

Reaction notes

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