1-Chloro-4-(chloromethyl)benzene → N-[6-(4-chlorobenzyloxy)-2-pyridyl]-3,4,5,6-tetrahydrophthalimide

HRID 1995841Notes

Reaction equation

HRID 1995841 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])[CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>C(=O)([O-])[O-].[Ag+2].C1C=CC=CC=1>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:1][C:2]2[N:7]=[C:6]([N:8]3[C:12](=[O:13])[C:11]4[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=4[C:9]3=[O:18])[CH:5]=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 178514957HCID 178514957, compound

Product 1

HCID 20486076N-[6-(4-chlorobenzyloxy)-2-pyridyl]-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent

Procedure

A mixture of N-(6-hydroxy-2-pyridyl)-3,4,5,6-tetrahydrophthalimide (3.9 g), silver carbonate (2.2 g), p-chlorobenzyl chloride (2.6 g) and benzene (75 ml) is stirred, in the dark, at 45° for about 72 hours. Then, the reaction is cooled and filtered. The filtrate is washed with 10% sodium bicarbonate and water, dried and stripped to give N-[6-(4-chlorobenzyloxy)-2-pyridyl]-3,4,5,6-tetrahydrophthalimide.

Workup

  1. temperatureThen, the reaction is cooled
  2. filtrationfiltered
  3. washThe filtrate is washed with 10% sodium bicarbonate and water
  4. customdried

Sources & evidence

ORD record
ord-7eb0b6cb479f4545a5acf7e04a9ecd27
Source dataset
uspto-grants-1983_09
Patent number
US04406689

Reaction notes

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