Water → HCID 11579422, compound

HRID 2363674Notes

Reaction equation

HRID 2363674 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([NH:14][CH2:15][CH:16]=[CH2:17])[CH:12]=[CH2:13].C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:14]([CH2:15][CH:16]=[CH2:17])[CH2:11][CH:12]=[CH2:13])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 31279Diallylamine

Product 1

HCID 11579422HCID 11579422, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoronitrobenzene (5.00 g, 35.44 mmol), diallylamine (3.48 g, 4.4 ml, 35.44 mmol) and K2CO3 (5.39 g, 38.98 mmol) in dry DMSO (40 ml) was heated at 100° C. under an atmosphere of argon for 3 h. The reaction mixture was then left to cool to room temperature (23° C.) and added to water (300 ml) and extracted with EtOAc (4×75 ml). The combined organics were washed with brine (100 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a red oil that was purified by chromatography (2:1 Hexane/DCM) to give the title compound (4.60 g, 59%) as an orange oil.

Workup

  1. waitThe reaction mixture was then left
  2. temperatureto cool to room temperature (23° C.)
  3. extractionextracted with EtOAc (4×75 ml)
  4. washThe combined organics were washed with brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed under reduced pressure
  7. customto give a red oil that
  8. customwas purified by chromatography (2:1 Hexane/DCM)

Sources & evidence

ORD record
ord-4fe3581bd214407da091a40a348182e1
Source dataset
uspto-grants-2014_04
Patent number
US08691979B2

Reaction notes

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