Pyridine → HCID 69812329, compound

HRID 1043711Notes

Reaction equation

HRID 1043711 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[CH:10]([S:13](Cl)(=[O:15])=[O:14])([CH3:12])[CH3:11].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][S:13]([CH:10]([CH3:12])[CH3:11])(=[O:15])=[O:14])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 824082-Propanesulfonyl chlorideHCID 30185263-Bromo-5-methylaniline

Product 1

HCID 69812329HCID 69812329, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-5-methylaniline (500 mg, 2.2 mmol) in DCM (5 mL), isopropylsulfonylchloride (0.3 mL, 2.7 mmol) was added, followed by the addition of pyridine (0.45 mL, 5.6 mmol). The reaction was stirred at room temperature for 25 hours at which time it was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), and absorbed onto silica. Purification by flash chromatography (SiO2, 0-30% EtOAc in hexanes) afforded N-(3-bromo-5-methylphenyl)propane-2-sulfonamide (558 mg, 1.9 mmol, 85%) as a peach colored solid: 1H NMR (400 MHz, CDCl3) δ 1.41 (d, J=6.7 Hz, 6H) 2.31 (s, 3H) 3.33 (m, 1H) 6.84 (br s, 1H) 6.97 (s, 1H) 7.10 (s, 1H) 7.21 (s, 1H).

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customabsorbed onto silica
  6. customPurification by flash chromatography (SiO2, 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-78da6b4637ef481f880a0b88ca524f2d
Source dataset
uspto-grants-2013_10
Patent number
US08563553B2

Reaction notes

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