Water → HCID 10003973, compound

HRID 1708391Notes

Reaction equation

HRID 1708391 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13]Br)[CH2:2][CH2:3][CH3:4].[C:16]1([C:22]2[N:23]=[C:24]([SH:33])[NH:25][C:26]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:1]([O:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][S:33][C:24]1[NH:25][C:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10016485HCID 10016485, compoundHCID 178527825HCID 178527825, compound

Product 1

HCID 10003973HCID 10003973, compoundYield 138.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-(2-butoxyethyl)-5-bromopentanamide (3.89 g, 13.9 mmol), 4,5-diphenyl-1H-imidazole-2-thiol (3.57 g, 14.2 mmol), potassium carbonate (2.38 g, 17.2 mmol) and tetra-n-butylammonium iodide (1.50 g, 4.06 mmol) were mixed in 100 mL anhydrous tetrahydrofuran, and heated to reflux for 18 hours. After cooling, the mixture was poured into water (400 mL). This mixture was extracted with ethyl acetate (2×400 mL), and the extracts were combined, dried over anhydrous magnesium sulfate and evaporated. The residue was eluted through a short plug of silica gel (ethyl acetate), and evaporation afforded sufficiently pure N-(2-butoxyethyl)-5-(4,5-diphenyl-1H-imidazol-2-ylthio)-pentanamide (8.69 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. temperatureAfter cooling
  4. extractionThis mixture was extracted with ethyl acetate (2×400 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. washThe residue was eluted through a short plug of silica gel (ethyl acetate), and evaporation

Sources & evidence

ORD record
ord-fbfdf8b8a8bd4c8c9a3b32f6e09c435a
Source dataset
uspto-grants-1994_10
Patent number
US05358946

Reaction notes

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