Water → HCID 71294751, compound

HRID 1019760Notes

Reaction equation

HRID 1019760 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([N+:12]([O-:14])=[O:13])=[CH:6][C:5]=1[Cl:15].C([N:18]([CH2:21]C)[CH2:19]C)C.[F:23][C:24]1[CH:31]=CC(CN)=[CH:26][CH:25]=1.O>CS(C)=O>[Cl:15][C:5]1[CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[C:8]([O:10][CH3:11])=[CH:9][C:4]=1[C:3]1[CH:31]=[C:24]([F:23])[CH:25]=[CH:26][C:2]=1[CH2:21][NH:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 67468969HCID 67468969, compound

Product 1

HCID 71294751HCID 71294751, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-(2-bromoethyl)-2-chloro-5-methoxy-4-nitrobenzene (7.0 g, 23.7 mmol) in DMSO (100 mL), triethylamine (8.25 mL, 59.2 mmol) and 4-fluorobenzylamine (3.56 g, 28.5 mmol) were added at room temperature and the mixture stirred for 5 hours. After completion of the reaction, water (500 mL) was added and the mixture was extracted with EtOAc (2×150 mL). The combined organic extracts were washed with water (100 mL), brine (100 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral silica gel using 15-20% EtOAc in hexane to give the title compound (1.5 g, 19%) as a solid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc (2×150 mL)
  3. washThe combined organic extracts were washed with water (100 mL), brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on neutral silica gel using 15-20% EtOAc in hexane

Sources & evidence

ORD record
ord-9ede75856fef495482d1e03987788c9f
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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