Ammonia → 1-Dodecyl-1H-imidazole

HRID 544501Notes

Reaction equation

HRID 544501 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH3:14].[CH:15]([CH:17]=O)=O.[CH2:19]=O>C(O)CC>[CH2:1]([N:13]1[CH:17]=[CH:15][N:14]=[CH:19]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 7860GlyoxalHCID 13583Dodecylamine

Product 1

HCID 780021-Dodecyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

92.5 parts of dodecylamine and 34 parts of 25% strength aqueous ammonia aredissolved in 100 parts of propanol and are added dropwise, in the course of30 minutes, simultaneously with a mixture of 72.5 parts of 40% strength aqueous glyoxal solution and 37.5 parts of 40% strength aqueous formaldehyde solution, to 200 parts of propanol at 80° C. The mixture is then stirred for a further 20 minutes. Working up by distillation gives 76.5 parts of N-dodecylimidazole (boiling point 152° C./2 mm Hg), corresponding to 64.8% of theory.

Workup

  1. distillationWorking up by distillation

Sources & evidence

ORD record
ord-79068ea6454a412e8f5dfdaa19d4e47a
Source dataset
uspto-grants-1984_05
Patent number
US04450277

Reaction notes

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