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Allyl bromide → HCID 22130396, compound

HRID 1857703
Notes
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Reaction equation

HRID 1857703 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26](Br)[CH:27]=[CH2:28].[OH-].[Na+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:28]([N:11]1[C:12]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=[C:10]1[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:27]=[CH2:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 178440141HCID 178440141, compound

Product 1

HCID 22130396HCID 22130396, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

In 10 ml of dry tetrahydrofuran was dissolved 744 mg (2.00 mmol) of 2-(benzyloxymethyl)-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazole (16e), followed by addition of 410 mg (2.40 mmol) of allyl bromide, 96 mg (2.40 mmol) of sodium hydroxide and 5 mg (0.015 mg) of tetrabutylammoniumbromide at room temperature with stirring, and the mixture was stirred at room temperature for 3 hours. This reaction mixture was concentrated under reduced pressure, the residue was extracted with methylene chloride, the organic layer was washed with water arid dried over sodium sulfate. The solvent was concentrated under reduced pressure and the residual oil was fractionated by silica gel chromatography (ethyl acetate: methylene chloride=1:9). From the first fraction, 50 mg (yield 6.7%) of the objective position isomer (17g') was obtained, and then, 480 mg (yield 58%) of 1-allyl-2-benzyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazole (17g) was obtained.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. concentrationThis reaction mixture was concentrated under reduced pressure
  3. extractionthe residue was extracted with methylene chloride
  4. washthe organic layer was washed with water arid
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-443df21f929e4bdeaedae7099eb15d1a
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06147097

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes