Methyl iodide → HCID 11041749, compound

HRID 491574Notes

Reaction equation

HRID 491574 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[N:7][NH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[O:4].[C:14](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[CH3:13][O:12][C:10]([C:9]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6][N:7]([CH3:14])[N:8]=1)=[O:11].[CH3:13][O:12][C:10]([C:9]1[N:8]=[N:7][N:6]([CH3:14])[C:5]=1[C:3]([O:2][CH3:1])=[O:4])=[O:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178499188HCID 178499188, compound

Product 2

HCID 11041749HCID 11041749, compoundYield 46%HCID 12574370Dimethyl 1-methyl-1H-1,2,3-triazole-4,5-dicarboxylateYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,2,3-Triazole-4,5-dicarboxylic acid dimethyl ester (Y. Tanaka et al. Tetrahedron 29, 3271 (1973)) (74.06 g; 0.40 mol), potassium carbonate (110.57 g; 0.80 mol) and methyl iodide (73.81 g; 0.52 mol) were reacted in acetonitrile (1000 ml) at 40° C. for 20 minutes and then for 20 hours at ambient temperature. The mixture was poured onto ice-water and extracted with ether to give the crude product (70.66 g) as a mixture of isomers. Separation on silica gel in ethyl acetate-hexane (2:3) yielded 36.51 g (46%) of 2-methyl-2H-1,2,3-triazole-4,5-dicarboxylic acid dimethylester [m.p. 86-87° C.; 1H-NMR (300 MHz, DMSO-d6), δ(ppm): 4.27(s,3H), 3.88(s,6H)] and 26.92 g (34%) of 1-methyl-1H-1,2,3-triazole-4,5-dicarboxylic dimethylester [m.p. 63-64° C.; 1H-NMR (300 MHz, DMSO-d6), δ(ppm): 4.19(s,3H), 3.93(s,3H), 3.87(s,3H)].

Workup

  1. additionThe mixture was poured onto ice-water
  2. extractionextracted with ether
  3. customto give the crude product (70.66 g)
  4. additionas a mixture of isomers
  5. customSeparation on silica gel in ethyl acetate-hexane (2:3)

Sources & evidence

ORD record
ord-6393caeafc9d44338ee78fefa519e11b
Source dataset
uspto-grants-2009_05
Patent number
US07531559B2

Reaction notes

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