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Benzyl Bromide → 1-benzyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole

HRID 1415997
Notes
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Reaction equation

HRID 1415997 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH2:15][O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[N:12][C:11]=2[CH:26]([CH3:28])[CH3:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:29]([N:14]1[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:26]([CH3:28])[CH3:27])[N:12]=[C:13]1[CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 178491401HCID 178491401, compound

Product 1

HCID 221309361-benzyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazoleYield 88%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium Bromide
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

(1)In 10 ml of dry tetrahydrofuran was dissolved 423 mg (1.00 mmol)of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (16b), followed by addition of 205 mg (1.20 mmol)of benzyl bromide, 48 mg (1.2 mmol)of sodium hydroxide and 5 mg (0.015 mg)of tetrabutylammonium bromide at room temperature with stirring, and the mixture was stirred at the same temperature for 3 hours. This reaction mixture was concentrated under reduced pressure and the residue was diluted with water and extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure and the residual oil was fractionated by silica gel chromatography (ethyl acetate:methylene chloride=1:9). From the first fraction, 33 mg (yield 6.5%)of the objective position isomer (17f')was obtained. From the subsequent fraction, 450 mg (yield 88%) of 1-benzyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (17f)was obtained.

Workup

  1. stirringthe mixture was stirred at the same temperature for 3 hours
  2. concentrationThis reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customFrom the first fraction, 33 mg (yield 6.5%)of the objective position isomer (17f')was obtained

Sources & evidence

ORD record
ord-c1890c22b24c4ac6ad67102c668cd28a
Source dataset
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05910506

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes