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Tetrahydrofuran → 2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-p-nitrobenzyl-1H-imidazole

HRID 1857760
Notes
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Reaction equation

HRID 1857760 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[NH:12][C:13]([S:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[N+:30]([CH:33](Br)[C:34]1C=CC=C[CH:35]=1)([O-:32])=[O:31].O1[CH2:45][CH2:44][CH2:43][CH2:42]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:42][C:43]2[CH:35]=[CH:34][C:33]([N+:30]([O-:32])=[O:31])=[CH:45][CH:44]=2)[C:13]([S:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11356361NitrobenzylbromideHCID 178440093HCID 178440093, compound

Product 1

HCID 178907742-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-p-nitrobenzyl-1H-imidazoleYield 93%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

In 10 ml of tetrahydrofuran was dissolved 1.05 mg (2.5 mmol) of 2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (Compound I-136), followed by addition of 220 mg (5.5 mmol) of sodium hydroxide, 48 mg (0.15 mmol) of tetrabutylammonium bromide and 594 mg (2.75 mmol) of nitrobenzylbromide with stirring at room temperature, and the mixture was reacted for 3 hours and worked up. The reaction mixture was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with water, dried, and the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate:chloroform=1:9) to give 1.3 g (93%) of 2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-p-nitrobenzyl-1H-imidazole (125a) as oil.

Workup

  1. customthe mixture was reacted for 3 hours
  2. distillationThe reaction mixture was distilled off under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:chloroform=1:9)

Sources & evidence

ORD record
ord-dfac2af144234dc0ae711ae44a77de7b
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