Ethyl Acetate → HCID 11398805, compound

HRID 1661919Notes

Reaction equation

HRID 1661919 reaction equation
[Br:1]Br.[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([CH2:17][CH2:18][O:19][CH3:20])[C:15]3[C:21]([O:35][CH3:36])=[CH:22][C:23]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[S:32]([CH3:34])=[O:33])=[CH:24][C:14]=3[N:13]=2)=[CH:8][CH:7]=1)([CH3:5])[CH3:4].CCOC(C)=O>C(O)(=O)C>[Br:1][C:24]1[C:14]2[N:13]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([CH:3]([CH3:5])[CH3:4])=[CH:7][CH:8]=3)[N:16]([CH2:17][CH2:18][O:19][CH3:20])[C:15]=2[C:21]([O:35][CH3:36])=[CH:22][C:23]=1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]([CH3:34])=[O:33]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 57772021HCID 57772021, compound

Product 1

HCID 11398805HCID 11398805, compoundYield 501.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

53 μl (0.122 mmol) bromine are added to a solution of 496 mg (1.03 mmol) 2-(4-isopropyl-phenyl)-5-(2-methanesulfinyl-benzyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole in 22 ml glacial acetic acid. The reaction mixture is stirred at room temperature for 10 min. Then 25 ml EtOAc are added and this solution is washed with 4N NaOH (2×), water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=1:4) to afford 340 mg of the title compound as colorless crystals.

Workup

  1. washthis solution is washed with 4N NaOH (2×), water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=1:4)

Sources & evidence

ORD record
ord-e424f6deab6a4e879475274529b3cdb5
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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