Diphenylphosphinic chloride → 2,4-Dimethyl-6-[2-(4-geranyloxybenzoylamino)ethylamino]pyridine

HRID 342672Notes

Reaction equation

HRID 342672 reaction equation
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:36][CH2:37][CH2:38][NH:39][C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[N:41]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:47][C:42]1[CH:43]=[C:44]([CH3:46])[CH:45]=[C:40]([NH:39][CH2:38][CH2:37][NH:36][C:16](=[O:18])[C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])=[CH:20][CH:19]=2)[N:41]=1

Participants

6

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 123615004-Geranyloxybenzoic acidHCID 193637922-(2-Aminoethylamino)-4,6-dimethylpyridine

Product 1

HCID 193637882,4-Dimethyl-6-[2-(4-geranyloxybenzoylamino)ethylamino]pyridineYield 78.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

4-geranyloxybenzoic acid(2.30 g) was dissolved in chloroform(50 ml) and triethylamine(2.33 ml), and then diphenylphosphinic chloride(1.48 ml) was added thereto while being cooled with ice. After being stirred for 45 minutes, the mixture, with 2-(2-aminoethylamino)-4,6-dimethylpyridine(1.90 g) added thereto, was stirred for 3 hours at room temperature. The reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1). The resulting solid was recrystallized from n-hexane/ethyl acetate, thereby yielding 2.79 g of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 3 hours at room temperature
  3. washThe reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  7. customThe resulting solid was recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-0cc1e92ce4db4c74aec2b6c07f303bb3
Source dataset
uspto-grants-1999_01
Patent number
US05859032

Reaction notes

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