Hydrochloric Acid → 1-Cyclobutyl-1H-imidazole-4-carboxylic acid hydrochloride

HRID 82304노트

반응식

HRID 82304 반응식
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]1

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 866721321-cyclobutyl-1H-imidazole-4-carboxylic acid ethyl ester

생성물 1

HCID 708176011-Cyclobutyl-1H-imidazole-4-carboxylic acid hydrochloride수율 88%

실험 절차

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]+.

후처리

  1. temperaturerefluxed for 1 day
  2. concentrationThe solution was concentrated to dryness in vacuo
  3. customThe solid was azeotroped with toluene
  4. customtriturated with toluene
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-d3cc5ec4ae7e4e8fbd87dc30d2356eb0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

반응 노트

불러오는 중…