N-methyl-2-pyrrolidone → HCID 59620855, compound

HRID 1634862Notes

Reaction equation

HRID 1634862 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.C([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20]C=2)[CH:16]=[CH:15][CH:14]=1)CCCC.[NH2-].[Na+].ClC[C:27]1[CH:34]=[CH:33]C(C=C)=[CH:29][CH:28]=1>[I-].[Na+].C(C1C=C(O)C(C(C)(C)C)=CC=1O)(C)(C)C.C(Cl)(Cl)Cl>[CH:34]([C:27]1[CH:3]=[CH:4][C:5]([CH2:6][NH:2][C:1]2[C:22]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=2)=[CH:29][CH:28]=1)=[CH2:33]

Participants

8

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 24533Sodium amideHCID 74126p-Vinylbenzyl chlorideHCID 5187321-Pentylnaphthalene

Product 1

HCID 59620855HCID 59620855, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 23742,5-Di-tert-butylhydroquinoneCatalystHCID 5238Sodium IodideCatalystHCID 6212ChloroformSolvent

Procedure

Into 120 g of N-methyl-2-pyrrolidone were dissolved 11.5 g of 1-amylnaphthalene, and then 3.74 g of sodium amide were added to the resultant solution while the solution was stirred at room temperature. Into the solution were added 1.20 g of sodium iodide as a catalyst and 0.89 g of 2,5-di-t-butylhydroquinone as a polymerization inhibitor. Thereafter, 13.4 g of p-chloromethylstyrene were added thereto over 30 minutes. The resultant solution was stirred at room temperature for 2 hours, and then 200 ml of chloroform were added thereto and dissolved. The solution was washed 3 times with water. The solvent was removed from the chloroform phase. The residue was purified by column chromatography to yield 11.6 g of p-vinylbenzylnaphthylamine as an intermediate.

Workup

  1. dissolutiondissolved
  2. washThe solution was washed 3 times with water
  3. customThe solvent was removed from the chloroform phase
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-111a2351233e4c91b934c98ea48eb507
Source dataset
uspto-grants-2003_01
Patent number
US06509125B1

Reaction notes

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