Benzene, (3-chloro-1-propenyl)- → 1-(Vinylbenzyl)-3-((S)-alpha-methylbenzylcarbamoyl)-pyridinium chloride

HRID 65471

Reaction equation

HRID 65471 reaction equation
[CH3:1][C@H:2]([NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:18][CH2:19][CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[Cl-:18].[CH:20]([CH:21]([N+:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:10](=[O:17])[NH:9][C@@H:2]([CH3:1])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:12]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH2:19]

Participants

4

Reactant 2

HCID 94242Benzene, (3-chloro-1-propenyl)-HCID 765754N-((S)-alpha-methylbenzyl)nicotinamide

Product 1

HCID 704518671-(Vinylbenzyl)-3-((S)-alpha-methylbenzylcarbamoyl)-pyridinium chlorideYield 89.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A 100 ml methanol solution containing 2.26 g (1.00×10-2 mols) of N-((S)-α-methylbenzyl)nicotinamide was charged into a 250 ml round bottom flask equipped with condenser, addition funnel, drying tube, nitrogen purge and magnetic stirrer. To this stirred reaction mixture was added, dropwise over a 10 minute interval, 50 ml of a methanol solution containing 1.53 g (1.00×10-2 mols) of chloromethylstyrene. The solution was stirred for 24 hours at 25° C., then was concentrated under vacuum to afford solid which was recrystallized from methanol to yield 3.40 g (8.98×10-3 mols) of product.

Workup

  1. additionwas charged into a 250 ml round bottom flask
  2. customequipped with condenser, addition funnel
  3. customdrying tube
  4. customnitrogen purge
  5. customTo this stirred reaction mixture
  6. concentrationwas concentrated under vacuum
  7. customto afford solid which
  8. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-5f8417b8409e4cb6abf2aaa05ff224db
Source dataset
uspto-grants-1986_09
Patent number
US04614770

Linked notes

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