Chloromethyl acetate → 1-(Acetyloxymethyl)-3-(dimethylcarbamoyloxy)pyridinium chloride

HRID 543156Notes

Reaction equation

HRID 543156 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]([O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:4].[C:13]([O:16][CH2:17][Cl:18])(=[O:15])[CH3:14]>C(OCC)C>[Cl-:18].[C:13]([O:16][CH2:17][N+:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][C:3](=[O:4])[N:2]([CH3:12])[CH3:1])[CH:7]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 69366Chloromethyl acetateHCID 98821Norpyridostigmine

Product 1

HCID 138819501-(Acetyloxymethyl)-3-(dimethylcarbamoyloxy)pyridinium chlorideYield 93.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Dimethylcarbamoyloxypyridine (1.66 g) and chloromethyl acetate (2.18 g) were stirred at 90° C. for 1 hr. The hot reaction mixture was poured into 100 ml of anhydrous diethylether with vigorous stirring. The supernatant was removed by decantation followed by addition of 500 ml of diethylether. Again, the supernatant was removed by decantation. These procedures were repeated three times. The solvent was removed under reduced pressure to give 2.56 g of 1-(acetyloxymethyl)-3-(dimethylcarbamoyloxy)pyridinium chloride as oil. The structure was determined by N.M.R.

Workup

  1. customThe supernatant was removed by decantation
  2. additionfollowed by addition of 500 ml of diethylether
  3. customAgain, the supernatant was removed by decantation
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7ef6bae101fb49ba8a089e1413a13140
Source dataset
uspto-grants-1987_04
Patent number
US04661502

Reaction notes

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