Triethylamine → N-(2-chlorophenethyl)-2-nitrobenzenesulfonamide

HRID 333994Notes

Reaction equation

HRID 333994 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH2:10].C(N(CC)CC)C.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28])([O-:20])=[O:19]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N+:18]([O-:20])=[O:19])(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 831172-(2-Chlorophenyl)ethylamine

Product 1

HCID 86699359N-(2-chlorophenethyl)-2-nitrobenzenesulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 mL of 2-(2-chlorophenyl)ethylamine and 1.2 mL of triethylamine were dissolved in 50 mL of dichloromethane. To the solution, 1.6 g of 2-nitrobenzenesulfonyl chloride was added at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed with saturated saline, and the organic layer was separated and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 2.3 g of the title compound as a pale yellow crystalline solid (92%).

Workup

  1. washThe reaction solution was washed with saturated saline
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8136b5d4a0404b25b3306056c04aa9a6
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

Loading…