Ammonia → N-Octyl imidazole

HRID 544500Notes

Reaction equation

HRID 544500 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH3:10].[CH:11]([CH:13]=O)=O.[CH2:15]=O>C(O)CC>[CH2:1]([N:9]1[CH:13]=[CH:11][N:10]=[CH:15]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 7860GlyoxalHCID 8143Octylamine

Product 1

HCID 161351N-Octyl imidazoleYield 71.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

64.6 parts of n-octylamine and 34 parts of 25% strength aqueous ammonia aredissolved in 186 parts of propanol and are introduced dropwise over 30 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, into a stirred flask. The temperature is kept at 65° C. After all has been introduced, stirring is continued for 20 minutes at 65° C., and the mixture is then worked up by distillation. 64.2 parts of 1-octylimidazole (boiling point 110° C./1 mm Hg) are obtained, corresponding to a yield of 71.3% of theory.

Workup

  1. customis kept at 65° C
  2. additionAfter all has been introduced
  3. distillationthe mixture is then worked up by distillation

Sources & evidence

ORD record
ord-d01d13adc787434495f27302d75c1895
Source dataset
uspto-grants-1984_05
Patent number
US04450277

Reaction notes

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