Ammonia → 1-Phenylimidazole

HRID 544499Notes

Reaction equation

HRID 544499 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:8].[CH:9]([CH:11]=O)=O.[CH2:13]=O>C(O)CC>[C:2]1([N:1]2[CH:11]=[CH:9][N:8]=[CH:13]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 6115AnilineHCID 7860Glyoxal

Product 1

HCID 815951-PhenylimidazoleYield 70%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

A mixture of 93.1 parts of aniline and 68 parts of 25% strength aqueous ammonia in 100 parts of propanol, and a mixture of 145 parts of 40% strength aqueous glyoxal solution and 75 parts of 40% strength aqueous formaldehyde solution are simultaneously stirred into 200 parts of propanol in the course of 30 minutes, at 80° C. The mixture is thenkept at 80° C. for a further 30 minutes. Thereafter the solvent is stripped off under reduced pressure and the residue is subjected to fractional distillation. 100.9 parts of N-phenylimidazole (boiling point 128° C./2 mm Hg) are obtained, corresponding to a yield of 70.0%.

Workup

  1. distillationthe residue is subjected to fractional distillation

Sources & evidence

ORD record
ord-0a84ecbfc2464ca5b39a49fc7ac16a0e
Source dataset
uspto-grants-1984_05
Patent number
US04450277

Reaction notes

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