Dimethyl Sulfoxide → HCID 67264906, compound

HRID 1685161Notes

Reaction equation

HRID 1685161 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[K+].CS(C)=O.Cl.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]Cl>CC(=O)OCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[CH:11][N:12]([CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 178505533HCID 178505533, compound

Product 1

HCID 67264906HCID 67264906, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Charge a round bottom flask with 4-(3-chloro-4-fluoro-phenyl)-1H-imidazole (1.85 g; 1.00 equiv; 9.41 mmol), KOH (3.00 equiv; 28.23 mmol; 1.58 g, crushed to a fine powder), in DMSO (281.56 mmol; 20.00 mL). Add 2-dimethylaminoethyl chloride hydrochloride (1.20 equiv; 11.29 mmol; 1.63 g) in one portion and the solution becomes yellow. Heat at 45° C. for 2 days. Dilute the reaction with EA and wash with water, brine and dry the organics over MgSO4; filter, and concentrate to an orange oil. Purify the crude with ISCO chromatography over a Biotage 40M column eluting with a gradient of 5% MeOH/DCM to 10% MeOH/DCM at a flow rate of 40 mL/min to give the title compound (1.09 g; 4.07 mmol; 43.27%) as a light orange oil. MS(ES): (m/z)=268.0 (M+H).

Workup

  1. additionDilute
  2. washwash with water, brine
  3. dry with materialdry the organics over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate to an orange oil
  6. customPurify the crude with ISCO chromatography over a Biotage 40M column
  7. washeluting with a gradient of 5% MeOH/DCM to 10% MeOH/DCM at a flow rate of 40 mL/min

Sources & evidence

ORD record
ord-408c6784540a43f19c144068b9c42db5
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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