Potassium Carbonate → HCID 67442066, compound

HRID 1400882Notes

Reaction equation

HRID 1400882 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[CH2:7]([O:9][CH:10]([O:13][CH2:14][CH3:15])[CH2:11]Br)[CH3:8].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[CH2:7]([O:9][CH:10]([O:13][CH2:14][CH3:15])[CH2:11][N:5]1[CH:6]=[C:2]([I:1])[N:3]=[CH:4]1)[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 178506559HCID 178506559, compound

Product 1

HCID 67442066HCID 67442066, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 4-iodoimidazole (10 g, 51.6 mmol) and bromoacetaldehyde diethyl acetal (9.31 mL) in DMSO (30 mL) was added K2CO3 (10.69 g, 77 mmol). The reaction mixture was heated at 110° C. for 16 h. After cooling to RT, the reaction mixture was diluted with water and extracted with AcOEt. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Biotage (SNAP 80 g cartridge; AcOEt/Hex:0/100 to 50/50 over 20 CV). The desired fractions were collected and concentrated to afford title compound 260 (11.29 g, 36.4 mmol, 71% yield) as yellow oil. MS (m/z): 310.97 (M+H).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with AcOEt
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by Biotage (SNAP 80 g cartridge; AcOEt/Hex:0/100 to 50/50 over 20 CV)
  9. customThe desired fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-eea475516381440aae3c793495a1e769
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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