Water → 2-(2-Chloro-4-nitrophenyl)-N-(3-chlorobenzyl)ethanamine

HRID 1019741Notes

Reaction equation

HRID 1019741 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[Cl:13].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][NH2:19].O>CS(C)=O>[Cl:13][C:5]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][NH:19][CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([Cl:14])[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77802Benzenemethanamine, 3-chloro-HCID 183167611-(2-Bromoethyl)-2-chloro-4-nitrobenzene

Product 1

HCID 674691702-(2-Chloro-4-nitrophenyl)-N-(3-chlorobenzyl)ethanamineYield 71.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-(2-bromoethyl)-2-chloro-4-nitrobenzene (0.6 g, 1.84 mmol) in DMSO (20 mL), 3-chlorobenzylamine (1.21 g, 4.61 mmol) was added at room temperature. The reaction mixture was stirred for 3 hours at room temperature. After the completion of reaction, water (80 mL) was added and reaction mass was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and the solvents removed under reduced pressure. The product was purified by column chromatography on neutral silica gel using 5-15% EtOAc in hexane to give the title compound (0.43 g, 55%) as a solid.

Workup

  1. additionwas added
  2. customreaction mass
  3. extractionwas extracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. customthe solvents removed under reduced pressure
  6. customThe product was purified by column chromatography on neutral silica gel using 5-15% EtOAc in hexane

Sources & evidence

ORD record
ord-dde30032e37c4ad3aa1f5db724f1f0ce
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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