Potassium Carbonate → HCID 178527407, compound

HRID 277169Notes

Reaction equation

HRID 277169 reaction equation
[CH2:1]([S:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[N:18](S(=O)(=O)N(C)C)[C:17]([Si](C(C)(C)C)(C)C)=[N:16][CH:15]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-:33].[K+].[K+].C(S)CC1C=CC=CC=1.[Cl-].[Na+].[OH2:49]>CN(C)C=O>[NH:16]1[CH:15]=[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][S:9]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)(=[O:33])=[O:49])[N:18]=[CH:17]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 781262-PhenylethanethiolHCID 18314035HCID 18314035, compoundHCID 57417360Sodium chloride; water

Product 1

HCID 178527407HCID 178527407, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)imidazol-5-yl]butyl phenethyl sulfide. To a suspension of the product from step b (701 mg, 1.71 mmol) and potassium carbonate (283 mg, 2.05 mmol) in N,N-dimethylformamide (3 ml) was added phenethyl mercaptan (229 μl, 1.71 mmol). The reaction was stirred at room temperature for 6 h before the addition of brine (10 ml). The product was extracted with ethyl acetate (2×20 ml) and the combined organic material washed with water (3×20 ml) before drying over magnesium sulfate. Filtration and evaporation of the filtrate furnished the title compound as a pale yellow oil in quantitative yield: 1H NMR (300 MHz, CDCl3) 7.33-7.20 (5H, m), 6.95 (1H, s), 2.98-2.70 (6H, m), 2.78 (6H, s), 2.58 (2H, t), 1.76-1.73 (4H, m), 1.01 (9H, s), 0.39 (6H, s).

Workup

  1. extractionThe product was extracted with ethyl acetate (2×20 ml)
  2. washthe combined organic material washed with water (3×20 ml)
  3. dry with materialbefore drying over magnesium sulfate
  4. filtrationFiltration and evaporation of the filtrate

Sources & evidence

ORD record
ord-51fe967011eb4269ad302f13e1fe8c44
Source dataset
uspto-grants-2002_03
Patent number
US06355665B1

Reaction notes

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