Hydrochloric Acid → 1-Cyclobutyl-1H-imidazole-4-carboxylic acid hydrochloride
Reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[CH:10]=1)=[O:5])C.[ClH:15]>>[ClH:15].[CH:11]1([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[CH:8]2)[CH2:12][CH2:13][CH2:14]1Participants
Procedure
Ethyl 3-(dimethylamino)-2-isocyanoacrylate (WO 2007042545) (45 g, 0.27 mol) was added to cyclobutylamine (50 g, 0.70 mol) and heated to reflux for 2 hours. The solution was then cooled and concentrated. The residue was purified by column chromatography over silica gel (3:1 EtOAc:Heptane). The oily residue was triturated with TBME:heptane (1:1) and the resulting solid was collected and dried, giving 1-cyclobutyl-1H-imidazole-4-carboxylic acid ethyl ester (35 g, 67%, second crop not harvested). 1-Cyclobutyl-1H-imidazole-4-carboxylic acid ethyl ester (35 g, 0.21 mol) was dissolved in 6 N HCl (300 mL) and refluxed for 1 day. The solution was concentrated to dryness in vacuo. The solid was azeotroped with toluene, triturated with toluene and then dried under vacuum, giving the title compound 88% yield, 37.2 g, m/z 167 [M+H]+.
Workup
- temperaturerefluxed for 1 day
- concentrationThe solution was concentrated to dryness in vacuo
- customThe solid was azeotroped with toluene
- customtriturated with toluene
- customdried under vacuum
Sources & evidence
- ORD record
- ord-d3cc5ec4ae7e4e8fbd87dc30d2356eb0
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846698B2
Reaction notes
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