Water → ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoate

HRID 1033246Notes

Reaction equation

HRID 1033246 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 178489021HCID 178489021, compound

Product 1

HCID 10094797ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoateYield 103.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Part A. A suspension of 4,5-bis(4-methoxyphenyl)-2-mercapto-1H-imidazole (10.4 g, 33.2 mmol), ethyl 5-bromovalerate (5.00 mL, 31.6 mmol), potassium carbonate (5.50 g, 39.8 mmol), and tetra-n-butylammonium iodide (2 g) in tetrahydrofuran (100 mL) was heated to reflux for 20 hours. The mixture was cooled, and poured into water (400 mL). This was extracted with methylene chloride (2 ×400 mL), and the extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was purified by elution through a short plug of silica gel with ethyl acetate, and evaporation afforded ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoate (14.4 g, 32.6 mmol, 98%) as a waxy, low-melting solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe mixture was cooled
  4. extractionThis was extracted with methylene chloride (2 ×400 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual oil was purified by elution through a short plug of silica gel with ethyl acetate, and evaporation

Sources & evidence

ORD record
ord-298db64730b94ab5ab0f0411a5bc672e
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

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