HCID 59749542, compound → HCID 178435489, compound

HRID 1174692Notes

Reaction equation

HRID 1174692 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9]([C:11]([C:13]2[CH:22]=[CH:21][C:16]3[O:17][CH2:18][CH2:19][O:20][C:15]=3[CH:14]=2)=[CH2:12])[N:8]=[CH:7]1)(=O)=O.[H][H]>CCO.[Pd]>[O:17]1[C:16]2[CH:21]=[CH:22][C:13]([CH:11]([C:9]3[N:8]=[CH:7][NH:6][CH:10]=3)[CH3:12])=[CH:14][C:15]=2[O:20][CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 59749542HCID 59749542, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178435489HCID 178435489, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[1-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-vinyl]-imidazole-1-sulfonic acid dimethylamide (Intermediate-J1) (0.25 g, 0.75 mmol) in EtOH (10 mL) was reduced with 10% Pd/C catalyst (25 mg) under 40 psi of hydrogen at rt for 2.5 h. The mixture was filtered through Celite. The solution was concentrated and the residue was dissolved in 1.5 M HCl (10 mL) and heated to reflux for 3 h. The mixture was cooled to rt and basified with sat solution of NaHCO3. The mixture was extracted with ethyl acetate (2×) and the organic solution was dried over Na2SO4, filtered and evaporated to give 4-[1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-ethyl]-1H-imidazole (Intermediate-J2) as a tan solid 0.14 g (87%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationThe solution was concentrated
  3. dissolutionthe residue was dissolved in 1.5 M HCl (10 mL)
  4. temperatureheated
  5. temperatureto reflux for 3 h
  6. extractionThe mixture was extracted with ethyl acetate (2×)
  7. dry with materialthe organic solution was dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-b2e0c0bd71cb47ed9782e5c4d3d41052
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

Loading…