Methylglyoxal → 1,4-Dimethylimidazole

HRID 1676854Notes

Reaction equation

HRID 1676854 reaction equation
[CH3:1][NH2:2].[CH2:3]([NH2:5])[CH3:4].[CH3:6][C:7]([CH:9]=O)=O.C(C=O)=O>>[CH3:1][N:2]1[CH:6]=[C:7]([CH3:9])[N:5]=[C:3]1[CH3:4].[CH3:1][N:2]1[CH:9]=[C:7]([CH3:6])[N:5]=[CH:3]1

Participants

6

Reactant 4

HCID 880MethylglyoxalHCID 6329MethylamineHCID 6341EthylamineHCID 7860Glyoxal

Product 2

HCID 1387331,4-DimethylimidazoleHCID 147178651,2,4-Trimethyl-1H-imidazole

Procedure

The same procedure as in Example 1 was performed except that 38 parts of methylamine (as a 40% aqueous solution) was used in lieu of ethylamine (as a 70% aqueous solution), and 87 parts of methyl glyoxal was used in lieu of glyoxal (as a 40% aqueous solution). After the dropwise addition, a mixture comprising 1,2,4-trimethylimidazole (a-3) and 1,4-dimethylimidazole (b-3) was obtained. The obtained mixture was analyzed with HPLC to find that the weight ratio of (a-3) to (b-3) was 80:20. The mixture was further purified by distillation under the temperature and pressure conditions of 110° C. and 1.0 kPA, and the weight ratio of (a-3) to (b-3) after the purification was 85:15 (M-11). The obtained mixture was treated in the same manner as in Example 1 to obtain a mixture comprising 1,2,3,4-tetramethylimidazolium tetrafluoroborate (hereinafter, referred to as “TeMI”) and 1,3,4-trimethylimidazolium tetrafluoroborate (hereinafter, referred to as “4TMI”). By the HPLC analysis, the weight ratio between them was found to be 85:15. 212 g of the obtained mixture comprising TeMI and 4TMI was dissolved in propylene carbonate homogeneously so as to adjust the total amount to 1 liter to prepare the electrolyte solution of the present invention.

Workup

  1. additionAfter the dropwise addition

Sources & evidence

ORD record
ord-61730ba8c73c4de9a18a8357c6ece048
Source dataset
uspto-grants-2011_08
Patent number
US08007680B2

Reaction notes

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