Pyridinium, 1-(2-ethoxy-2-oxoethyl)-, bromide (1:1) → N-(Ethoxycarbonylmethyl)pyridinium Tetraphenylborate

HRID 1614295Notes

Reaction equation

HRID 1614295 reaction equation
[Br-].[CH2:2]([O:4][C:5]([CH2:7][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6])[CH3:3].[C:14]1([B-:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+]>O>[C:33]1([B-:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1.[CH2:2]([O:4][C:5]([CH2:7][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 87028Pyridinium, 1-(2-ethoxy-2-oxoethyl)-, bromide (1:1)HCID 2723787Sodium Tetraphenylborate

Product 1

HCID 19432273N-(Ethoxycarbonylmethyl)pyridinium TetraphenylborateYield 45.11%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 24.61 grams (0.10 mol) of N-(ethoxycarbonylmethyl)pyridinium bromide in 100 milliliters of water, there was added a solution of 34.22 grams (0.10 mol) of sodium tetraphenylborate in 150 milliliters of water. The mixture was diluted with 1 liter of water and filtered. The solid collected was dissolved in methylene chloride, the water layer was separated and the organic layer was dried over MgSO4 and concentrated. Recrystallization from ethyl acetate yielded 21.9 grams of product (45.11% of theory); mp=150°-152° C.

Workup

  1. filtrationfiltered
  2. customThe solid collected
  3. dissolutionwas dissolved in methylene chloride
  4. customthe water layer was separated
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-1d4248cf4eca48c7a5a478a6817b58e0
Source dataset
uspto-grants-1993_03
Patent number
US05196538

Reaction notes

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