Potassium tert-butoxide → HCID 58158560, compound

HRID 2095828Notes

Reaction equation

HRID 2095828 reaction equation
Br[CH:2]([CH3:16])[CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:7].CC(C)([O-])C.[K+]>CN(C)C=O>[F:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]2[CH:2]([CH3:16])[CH2:3][CH2:4][NH:5][C:6]2=[O:7])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58158465HCID 58158465, compound

Product 1

HCID 58158560HCID 58158560, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(3-bromobutyl)-3-(4-fluorophenyl)urea (1750 mg, 6.1 mmol) in N,N-dimethylformamide (30 mL) was added potassium tert-butoxide (920 mg, 7.0 mmol), and the mixture was stirred at 50° C. for 6 hr. The solvent was evaporated under reduced pressure, and ethyl acetate/tetrahydrofuran and 6N aqueous hydrochloric acid solution were added to the residue. The aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3). The combined organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=50/50→100/0) to give the title compound (490 mg, 39%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and ethyl acetate/tetrahydrofuran and 6N aqueous hydrochloric acid solution
  2. additionwere added to the residue
  3. extractionThe aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3)
  4. washThe combined organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=50/50→100/0)

Sources & evidence

ORD record
ord-2feaca9eab3f40b29623361b67685c8d
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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