Methyl iodide → 1-Methyl-3-{N-[beta-(4-pivalyloxyphenyl)ethyl]}carbamoylpyridinium iodide

HRID 1719483Notes

Reaction equation

HRID 1719483 reaction equation
[C:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:18])=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:25][I:26]>CC(C)=O>[I-:26].[CH3:25][N+:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:17](=[O:18])[NH:16][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:9][CH:10]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 134734273-{N-[beta-(4-pivalyloxyphenyl)ethyl]}carbamoylpyridine

Product 1

HCID 134734291-Methyl-3-{N-[beta-(4-pivalyloxyphenyl)ethyl]}carbamoylpyridinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.63 g (5 mmol) of the product of Example 26 in 10 ml of acetone, 1.41 g (10 mmol) methyl iodide were added and the mixture was refluxed overnight while stirring. The acetone layer was separated by decantation and the yellowish, oily residue was crystallized from methanol/ether.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe acetone layer was separated by decantation
  3. customthe yellowish, oily residue was crystallized from methanol/ether

Sources & evidence

ORD record
ord-024d586fc6bc4ee8a328d95472e5f581
Source dataset
uspto-grants-1985_09
Patent number
US04540564

Reaction notes

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