Water → HCID 22015755, compound

HRID 8405Notes

Reaction equation

HRID 8405 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH:12]=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)C1C=CC=CC=1.O.C1(C)C=CC=CC=1>Cl>[OH:8][CH2:9][C:10]1[N:11]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH:12]=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 220157572-Benzyloxymethyl-4-isopropyl-1-(pyridin-4-yl)-1H-imidazole

Product 1

HCID 22015755HCID 22015755, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
85 °C

Procedure

The compound (5) (20.0 g, 62.2 mmol) was suspended in 35% aqueous hydrochloric acid (100 ml). The solution was heated at 85° C. and stirred for 1 hour. The reaction mixture was cooled down to room temperature and water (100 ml) and toluene (44 ml) were added thereto with stirring. The aqueous layer was separated and neutralized with 30% aqueous sodium hydroxide, to which ethyl acetate (30 ml) was added with stirring. The obtained slurry was filtered, washed with cold water and dried to yield 2-hydroxymethyl-4-isopropyl-1-(pyridin-4-yl)-1H-imidazole (9) (11.7 g). Yield 81.4%.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringwith stirring
  3. customThe aqueous layer was separated
  4. additionwas added
  5. stirringwith stirring
  6. filtrationThe obtained slurry was filtered
  7. washwashed with cold water
  8. customdried

Sources & evidence

ORD record
ord-817f567d751f49859e698e37d51e69b5
Source dataset
uspto-grants-2006_08
Patent number
US07087764B2

Reaction notes

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