2-Nitrobenzenesulfonyl chloride → HCID 69288393, compound

HRID 914764Notes

Reaction equation

HRID 914764 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][NH:2]2.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18])([O-:10])=[O:9].CCCCCC.CCOC(C)=O>C(Cl)Cl.C(N(CC)CC)C>[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([N:2]1[CH2:3][CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2)(=[O:19])=[O:18])([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 1388052-Azabicyclo[2.2.1]hept-5-eneHCID 21226206Ethyl acetate hexane

Product 1

HCID 69288393HCID 69288393, compoundYield 152%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Azabicyclo[2.2.1]hept-5-ene (52.5 g, 54 mmole), prepared as described in (J Am Chem. Soc., (1985) 107, 1768), 2-nitrobenzenesulfonyl chloride (119.6, 54 mmole), and triethylamine (75 mL, 0.54 mmole) were combined in methylene chloride (500 mL) under a nitrogen atmosphere and stirred for 16 hours. The reaction mixture was quenched with water (500 mL) and the phases separated. The organic phase was washed with 2M HCl (5×100 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (chloroform then hexane:EtOAc 95:5 to 8:2) to provide the title compound (23 g, 23% yield). MS (DCI/NH3) m/e 281 (M+H)+, 298 (M+NH4)+.

Workup

  1. customThe reaction mixture was quenched with water (500 mL)
  2. customthe phases separated
  3. washThe organic phase was washed with 2M HCl (5×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (chloroform

Sources & evidence

ORD record
ord-82c2c429ce2e470db624cdb610734343
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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