Methyl Chloride → N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]N,N-dimethylammonium Chloride

HRID 51990

Reaction equation

HRID 51990 reaction equation
[O:1]([C:8]([O:10][CH2:11][CH2:12][N:13]([CH2:15][CH2:16][O:17][C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH3:14])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](#N)C.C[Cl:31]>CCOCC>[Cl-:31].[O:1]([C:8]([O:10][CH2:11][CH2:12][N+:13]([CH2:15][CH2:16][O:17][C:18]([O:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:19])([CH3:27])[CH3:14])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6327Methyl ChlorideHCID 6342AcetonitrileHCID 19962809N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N-methylamine

Product 1

HCID 19962807N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]N,N-dimethylammonium Chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 500 ml autoclave liner are added N,N-bis[2-((phenoxycarbonyl)oxy)ethyl]-N-methylamine (20.20 g, 56.2 mmol) and acetonitrile (25 ml). The liner is placed in an autoclave and the solution is treated with methyl chloride gas at 85° C. and at a pressure of 60 psig. After 18 h, the cooled mixture is treated with ether (500 ml) precipitating 6 as a white powder, 19.16 g (83%): mp 148°-150° C.

Workup

  1. customprecipitating 6 as a white powder, 19.16 g (83%)

Sources & evidence

ORD record
ord-e9eb252494e64ae791903e712144d101
Source dataset
uspto-grants-1997_04
Patent number
US05616546

Linked notes

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