Hydrochloric Acid → 5-Propyl-1H-imidazole-4-carboxylic acid hydrochloride

HRID 1793118노트

반응식

HRID 1793118 반응식
C([O:3][C:4]([C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH2:11][CH2:12][CH3:13])=[O:5])C.[ClH:14]>O>[ClH:14].[CH2:11]([C:10]1[NH:9][CH:8]=[N:7][C:6]=1[C:4]([OH:5])=[O:3])[CH2:12][CH3:13]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 13548611Ethyl 5-propyl-1H-imidazole-4-carboxylate

생성물 1

HCID 695931715-Propyl-1H-imidazole-4-carboxylic acid hydrochloride수율 100%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

5-Propyl-1H-imidazole-4-carboxylic acid ethyl ester 2 (2.00 g; 11.0 mmol) and concentrated aqueous HCl (40 mL) were combined and heated to reflux with stirring for 24 h. After cooling to rt, the light tan solution was diluted with water (100 mL) and extracted with EtOAc. The aqueous layer was then evaporated under reduced pressure. The residue was dissolved in 2-propanol (20 mL) and cooled to −78 C. Upon addition of Et2O, a white precipitate formed. This material was collected by filtration and dried under vacuum to afford 2.10 g (100%) of 3. 1H NMR (DMSO-d6): δ 0.87 (t, 3H), 1.69 (m, 2H), 2.92 (t, 2H), 9.17 (s, 1H); 13C NMR (DMSO-d6): δ 13.9, 22.4, 26.4, 120.9, 135.7, 140.0, 160.7; Anal. calcd for C7H11ClN2O20.66(C3H9O)0.33(H2O): C, 45.67; H, 7.24; N, 11.84; Cl, 14.98; found: C, 45.27; H, 7.17; N, 11.86; Cl, 14.68.

후처리

  1. temperatureheated
  2. temperatureto reflux
  3. extractionextracted with EtOAc
  4. customThe aqueous layer was then evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 2-propanol (20 mL)
  6. temperaturecooled to −78 C
  7. additionUpon addition of Et2O
  8. customa white precipitate formed
  9. filtrationThis material was collected by filtration
  10. customdried under vacuum

출처 및 근거

ORD 기록
ord-e5f8271f05a748aca5b142ffca477532
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07078528B2

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