Acetonitrile → Ethyl 4-methyl-2-(naphthalen-1-yl)-1H-imidazole-5-carboxylate

HRID 1252371Notes

Reaction equation

HRID 1252371 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O=[C:14]([C:20](=O)[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(#[N:25])C>>[CH3:21][C:20]1[NH:25][C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[N:12][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 83551-NaphthalenemethanamineHCID 12260829Ethyl 2,3-dioxobutanoate

Product 1

HCID 53404405Ethyl 4-methyl-2-(naphthalen-1-yl)-1H-imidazole-5-carboxylate

Procedure

A mixture of 9.1 g of 1-naphthalenemethylamine, 8.4 g of 2,3-dioxobutyric acid, ethyl ester, (Z)-2-oxime and 115 ml of acetonitrile was refluxed for 5 hours and then cooled. The solid was collected, giving 7.0 g of 5-methyl-2-(1-naphthalenyl)-1H-imidazole-4-carboxylic acid, ethyl ester.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperaturecooled
  3. customThe solid was collected

Sources & evidence

ORD record
ord-67a6393867264316a505305509117e8d
Source dataset
uspto-grants-1988_05
Patent number
US04743586

Reaction notes

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