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

HRID 1793118Notes

Reaction equation

HRID 1793118 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e5f8271f05a748aca5b142ffca477532
Source dataset
uspto-grants-2006_07
Patent number
US07078528B2

Reaction notes

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