Triethylamine → N-2-(4-bromophenyl)ethyl 2-propanesulfonamide

HRID 720559Notes

Reaction equation

HRID 720559 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:18]([S:21](Cl)(=[O:23])=[O:22])([CH3:20])[CH3:19]>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH:8][S:21]([CH:18]([CH3:20])[CH3:19])(=[O:23])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 533915p-Bromophenethylamine

Product 1

HCID 21893403N-2-(4-bromophenyl)ethyl 2-propanesulfonamideYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10.0 g (50 mmol) of 4-bromophenethylamine and 7.6 mL (55 mmol) of triethylamine in 150 mL of dichloromethane was added a solution of 6.2 mL (55 mmol) of isopropylsulfonyl chloride in 40 mL of dichloromethane dropwise. The mixture was stirred at room temperature for 18 hr. The mixture was washed with 100 mL of 1N aqueous hydrochloric acid, the organic layer was separated and the aqueous layer extracted one time with 100 mL each of dichloromethane. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford 6.7 g (44%) of the title compound.

Workup

  1. washThe mixture was washed with 100 mL of 1N aqueous hydrochloric acid
  2. customthe organic layer was separated
  3. extractionthe aqueous layer extracted one time with 100 mL each of dichloromethane
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91ba4d1c164d4fa0ab02fd2140e750b9
Source dataset
uspto-grants-2006_11
Patent number
US07135487B2

Reaction notes

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