Allyl bromide → HCID 22130396, compound

HRID 1415999Notes

Reaction equation

HRID 1415999 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+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[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]

Participants

6

Reactant 3

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

Product 1

HCID 22130396HCID 22130396, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(1)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 and 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
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customFrom the first fraction, 50 mg (yield 6.7%)of the objective position isomer (17g')was obtained

Sources & evidence

ORD record
ord-f1fc6f5fc1c045fda2b19729e324f2e4
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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