Hydrochloric Acid → HCID 178442247, compound

HRID 1946957Notes

Reaction equation

HRID 1946957 reaction equation
[CH3:1][CH:2]([CH3:35])[CH:3]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:4][C:5]1[N:6]=[CH:7][N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1.Cl.[OH-].[Na+]>C(O)C.O>[CH3:1][CH:2]([CH3:35])[CH:3]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:4][C:5]1[N:6]=[CH:7][NH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 597427414-(3-methyl-2-phenyl-butyl)-1-trityl-1H-imidazole

Product 1

HCID 178442247HCID 178442247, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 4-(3-methyl-2-phenyl-butyl)-1-trityl-1H-imidazole (80 mg) at r.t. in ethanol (2 ml) under an argon atmosphere was added 2 N HCl (3 ml). The mixture (suspension) was heated to reflux (turning to a clear light yellow solution when reaching 90° C.) and stirred for 2 hours and 30 minutes, then cooled to r.t. and concentrated to leave a light brown sticky solid. This was taken up in H2O and basified to pH>12 by the addition of 4 N NaOH. The product was extracted with CH2Cl2/MeOH 9:1. The combined organics were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 85:15) to give 4-(3-methyl-2-phenyl-butyl)-1H-imidazole (8 mg) as colorless gum. MS (ISP): 215.4 ([M+H]+)

Workup

  1. temperatureThe mixture (suspension) was heated
  2. temperatureto reflux (
  3. customreaching 90° C.
  4. concentrationconcentrated
  5. customto leave a light brown sticky solid
  6. extractionThe product was extracted with CH2Cl2/MeOH 9:1
  7. dry with materialThe combined organics were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 85:15)

Sources & evidence

ORD record
ord-feafee03a0e648608939851688d612e6
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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