p-Bromophenethylamine → N-(4-bromophenethyl)-3-cyanobenzenesulfonamide

HRID 735679Notes

Reaction equation

HRID 735679 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[C:11]([C:13]1[CH:14]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1)#[N:12]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][S:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([C:11]#[N:12])[CH:14]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 533915p-BromophenethylamineHCID 28013603-Cyanobenzene-1-sulfonyl chloride

Product 1

HCID 57842726N-(4-bromophenethyl)-3-cyanobenzenesulfonamideYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(4-bromophenyl)ethanamine (600 mg, 3.13 mmol) and TEA (800 mg, 8 mmol) in THF (10 mL), was added a solution of 3-cyano-benzenesulfonyl chloride (580 mg, 2.88 mmol) in THF (10 mL) at 0° C. The mixture was stirred at rt for 2 h, quenched with water, and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-50% EtOAc in hexanes) gives 68A (708 mg, 71%). MS (ESI) m/z 365.3 (M+H)+.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe organic layer washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification via flash chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-11fa70f78f5845d8a77be0946f3467ff
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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