Hydrochloric Acid → HCID 18405330, compound

HRID 1018320Notes

Reaction equation

HRID 1018320 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[N:9]([CH3:23])[C:10]=1[CH2:11][CH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:5])C.[OH-].[K+].Cl>C(O)C>[C:13]12([CH2:12][CH2:11][C:10]3[N:9]([CH3:23])[C:8]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])=[N:7][C:6]=3[C:4]([OH:5])=[O:3])[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:21]3)[CH2:20]1)[CH2:22]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54339100HCID 54339100, compound

Product 1

HCID 18405330HCID 18405330, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-(2-adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carboxylic acid ethyl ester (397 mg, 0.98 mmol) in ethanol (30 ml) was added 2.0M potassium hydroxide solution (3.4 ml). The solution was heated at reflux for 16 h, cooled to 50° C. and acidified (1M hydrochloric acid, pH=3-4). The ethanol was evaporated, the residue was diluted with water (30 ml) and the product was extracted with DCM. The organic layer was dried (MgSO4) and the solvent was evaporated to afford the product as a white solid (351 mg, 95%). 1H NMR (300MHz, CDCl3) 7.41-7.27 (4H, m), 6.00 (1H, br s), 3.38 (3H, s), 3.01 (2H, m), 2.20 (3H, s), 2.01 (3H, s), 1.70 (6H, m), 1.61 (6H, s), 1.37 (2H, m).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 16 h
  3. customThe ethanol was evaporated
  4. additionthe residue was diluted with water (30 ml)
  5. extractionthe product was extracted with DCM
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a919cb924bdc495298e7ef24099c269d
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

Loading…