Ammonia → HCID 178438927, compound

HRID 1694784Notes

Reaction equation

HRID 1694784 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9]([CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH3:13])[N:8]=[C:7]1[Si](C(C)(C)C)(C)C)(=O)=O.N>Cl>[C:14]1([CH:11]([C:9]2[N:8]=[CH:7][NH:6][CH:10]=2)[CH2:12][CH3:13])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67277561HCID 67277561, compound

Product 1

HCID 178438927HCID 178438927, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To remove protecting groups the amount of 155 mg (0.38 mmol) 2-(tert-butyl-dimethyl-silanyl)-4-(1-phenyl-propyl)-imidazole-1-sulfonic acid dimethylamide was dissolved in 10 ml 1.5N hydrochloric acid and refluxed for 1 h. The cooled solution was adjusted to pH>8 with 25% aqueous ammonia and the solution was extracted with dichloromethane (2 times). The combined organic layers are dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1) to yield 71 mg (99%) rac-4-(1-phenyl-propyl)-1H-imidazole as off-white solid: MS (ISP): 187.1 ((M+H)+.).

Workup

  1. customTo remove
  2. temperaturerefluxed for 1 h
  3. extractionthe solution was extracted with dichloromethane (2 times)
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1)

Sources & evidence

ORD record
ord-68b5eed55a56430b880cb8707f32d7aa
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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