3-Hydroxyacetophenone → HCID 21193540, compound

HRID 1067660Notes

Reaction equation

HRID 1067660 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[H-].[Na+].[Si]([C:20]1[N:21]([S:30](=[O:35])(=[O:34])[N:31]([CH3:33])[CH3:32])[C:22]([CH2:25][CH2:26][CH2:27][CH2:28]Cl)=[CH:23][N:24]=1)(C(C)(C)C)(C)C.C(OCC)(=O)C.CO>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[CH3:32][N:31]([CH3:33])[S:30]([N:21]1[C:22]([CH2:25][CH2:26][CH2:27][CH2:28][O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=2)=[CH:23][N:24]=[CH:20]1)(=[O:34])=[O:35]

Participants

8

Reactant 4

HCID 84873-HydroxyacetophenoneHCID 24758Sodium hydrideHCID 21193612HCID 21193612, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 21193540HCID 21193540, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

2.87 g of 3-ethanoylphenol (21 mmol) in anhydrous DMF (30 ml) is cooled to 5° C. (ice bath) under an argon atmosphere, and 0.37 g of sodium hydride (60% suspension in mineral oil; 9.25 mmol) are then added. The mixture is stirred at 5° C. for 10 minutes and then at 20° C. for 2 hours. 0.70 g of 2-(t-butyldimethylsilyl)-5-(4-chlorobutyl)-1-(dimethylsulphamoyl)imidazole (1.85 mmol) (synthesized as described by R. C. Vollinga, W. M. P. B. Menge and H. Timmerman, Rec., Trav., Chem. Pays-Bas, 1993, 112, 123-125) and 45 mg of tetrabutylammonium iodide are added and the mixture is heated at 80° C. under argon for 3 days, then cooled to 20° C. and diluted with diethyl ether until the solution becomes cloudy. The resulting solid is filtered off and the filtrate evaporated to dryness in vacuo, giving a dark orange oil. The latter is subjected to column chromatography (SiO2; using an ethyl acetate/methanol mixture in the ratio 9:1) to give 1-(N,N-dimethyl-sulphamoyl)-5-[4(3-ethanoylphenoxy)butyl]imidazole in the form of a yellow oil.

Workup

  1. waitat 20° C. for 2 hours
  2. temperaturethe mixture is heated at 80° C. under argon for 3 days
  3. temperaturecooled to 20° C.
  4. filtrationThe resulting solid is filtered off
  5. customthe filtrate evaporated to dryness in vacuo
  6. customgiving a dark orange oil

Sources & evidence

ORD record
ord-a32db1648f08422ea0b525d9dbbe5955
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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