Pyridine → HCID 53825916, compound

HRID 1952806Notes

Reaction equation

HRID 1952806 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>ClCCl>[CH2:6]([N:1]([CH2:12][CH2:13][CH2:14][CH3:9])[CH2:2][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

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 15891Phenyl chloroformateHCID 54074666HCID 54074666, compound

Product 1

HCID 53825916HCID 53825916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.30 ml) and phenyl chlorocarbonate (0.35 ml) were added to a suspension of [2-(hydroxymethyl)phenyl]-N-octadecylformamide (1.38 g) in dichloromethane (10 ml) while being cooled with ice. After being stirred for 1 hours at room temperature, the reaction mixture, with chloroform added thereto, was washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and then concentrated. N,N-Di-n-butylethylenediamine (0.57 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 40 g, chloroform:methanol=50:1), thereby yielding 1.31 g of the aimed compound as white solid.

Workup

  1. temperaturewhile being cooled with ice
  2. washwas washed with saturated sodium hydrogencarbonate aqueous solution and water successively
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated
  5. additionN,N-Di-n-butylethylenediamine (0.57 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 40 g, chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-9c7c92f54f1548f8a0d901a045b1c3ac
Source dataset
uspto-grants-2000_09
Patent number
US06114325

Reaction notes

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