Diethyl Ether → HCID 21474192, compound

HRID 2294164Notes

Reaction equation

HRID 2294164 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=4[N:12]=[CH:11]3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([Mg]Br)C.CCOCC.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[C:29]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([N:10]3[C:14]4[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=4[N:12]=[CH:11]3)[CH:5]=2)[NH:1][CH:2]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 21474183HCID 21474183, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 21474192HCID 21474192, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-(indol-5-yl)-5-methylbenzimidazole (1.00 g, 4.04 mmol, 2.0 equivalents) in anhydrous benzene (10 mL) at 0° C. under nitrogen was added a solution of ethyl magnesium bromide in ether (3.0M, 1.33 mL, 4.00 mmol, 2.0 equivalents) dropwise, and the resulting reaction solution was stirred at 0° C. under nitrogen for 30 minutes. Then, benzoyl chloride (0.23 mL, 1.98 mmol) was added dropwise rapidly to the reaction solution, and the resulting mixture was stirred at room temperature under nitrogen for 30 min. A saturated solution of sodium hydrogen carbonate (25 mL) was then added to the reaction mixture, and the resulting aqueous mixture was extracted with ethyl acetate (2×25 mL). The extracts were combined, dried (MgSO4), and evaporated under reduced pressure. The residue (2.1 g) was column chromatographed using silica gel (approximately 100 g) and eluted with ethyl acetate/hexanes (1:1) to afford the title compound (0.045 g, 0.13 mmol, 6%) as a white foam. Rf =0.65 in ethyl acetate/hexanes (1:1); 1H NMR (CD3OD) d 8.05-7.95 (m, 3H), 7.81 (d, J=6.8 Hz, 1H), 7.71 (d, J=8.5 Hz, 1H), 7.61-7.39 (m, 7H), 7.18 (d, J=8.4 Hz, 1H), 2.48 (s, 3H); FAB LRMS (m/z, relative intensity) 352 ([MH]+, 78%), 248 ([MH]+ --Ph(CO), 100).

Workup

  1. customthe resulting reaction solution
  2. stirringthe resulting mixture was stirred at room temperature under nitrogen for 30 min
  3. extractionthe resulting aqueous mixture was extracted with ethyl acetate (2×25 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customchromatographed
  7. washeluted with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-0aca00dd60b84db5b81891e2b8c7c574
Source dataset
uspto-grants-1997_11
Patent number
US05688809

Reaction notes

Loading…