Pyridine → HCID 46021782, compound

HRID 386474Notes

Reaction equation

HRID 386474 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>ClCCl>[CH2:1]([N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)[S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 9965096N-Benzyl-3-bromoaniline

Product 1

HCID 46021782HCID 46021782, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl-(3-bromo-phenyl)-amine (2 g, 7.6 mmol), benzenesulphonyl chloride (3.2 ml, 25 mmol) and pyridine (2.2 ml, 27.5 mmol) in dry dichloromethane (50 ml) were heated to reflux for 15 hrs. The reaction mixture was cooled to room temperature, quenched with water and extracted with dichloromethane (3×75 ml). The organics were combined, dried (magnesium sulphate) and concentrated in vacuo. The crude residue was then purified by column chromatography eluting with dichloromethane to afford the title compound as a white solid (1.45 g, 47%). HPLC retention time 4.93 mins. Mass spectrum (ES+) m/z 402 (M+H).

Workup

  1. temperatureto reflux for 15 hrs
  2. customquenched with water
  3. extractionextracted with dichloromethane (3×75 ml)
  4. dry with materialdried (magnesium sulphate)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was then purified by column chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-74a1c998714c4b95941b539210ae858f
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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