Triethylamine → Triethylmethylammonium methyl carbonate

HRID 566617Notes

Reaction equation

[C:1](=[O:6])([O:4]C)[O:2][CH3:3].[CH2:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH3:8]>>[CH3:3][O:2][C:1](=[O:4])[O-:6].[CH2:7]([N+:9]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH3:1])[CH3:8]

Participants

Reactant 2

HCID 8471Triethylamine

HCID 12021Dimethyl Carbonate2×

Product 1

HCID 11019667Triethylmethylammonium methyl carbonateYield 89.9%

Procedure

From EP-A-291 074, it is known that dimethyl carbonate acts as a methylating agent during its reaction with an approximately stoichiometric amount of a tertiary amine. Thus, for example, the reaction of triethylamine with dimethyl carbonate gives the product triethylmethylammonium methyl carbonate in 89.9% yield (loc. cit., Example 1).

Sources & evidence

ORD record: ord-0bcf6a5ab3f3440f957193b69aaaa4b4
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06175019B1

Reaction notes

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