Hydrochloric Acid → 1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(3-phenylpropyl)-

HRID 1857744Notes

Reaction equation

HRID 1857744 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([S:11][C:12]2[NH:16][C:15]([CH2:17][O:18]CC3C=CC(OC)=CC=3)=[N:14][C:13]=2[CH:28]([CH3:30])[CH3:29])[CH:7]=[C:8]([Cl:10])[CH:9]=1.Br[CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl>O.C(O)C.O1CCCC1>[Cl:10][C:8]1[CH:7]=[C:6]([S:11][C:12]2[N:16]([CH2:32][CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:15]([CH2:17][OH:18])=[N:14][C:13]=2[CH:28]([CH3:29])[CH3:30])[CH:5]=[C:4]([Cl:3])[CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 178491401HCID 178491401, compound

Product 1

HCID 4740381H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(3-phenylpropyl)-Yield 40%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To dry tetrahydrofuran was added 40 mg of 60% sodium hydride, and under ice-cooling, 200 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (101b) was added. After 20 minutes, 136 μl of 1-bromo-3-phenylpropane was added. After stirred at room temperature for 3 hours, the mixture was diluted with water and extracted with diethyl ether. The extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. To thus-obtained oil were added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, and the mixture was stirred at 90° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give 80 mg of Compound I-122 (yield 40%).

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with diethyl ether
  3. dry with materialThe extract was dried over sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customTo thus-obtained oil
  6. stirringthe mixture was stirred at 90° C. for 2 hours
  7. customAfter completion of the reaction
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionan aqueous sodium hydrogen carbonate solution was added
  10. extractionextracted with ethyl acetate
  11. dry with materialThe extract was dried over sodium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-39b0a118b55c45678a09a92dbb2eb4c9
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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