2-Nitrobenzenesulfonyl chloride → HCID 117697629, compound

HRID 1778522Notes

Reaction equation

HRID 1778522 reaction equation
Cl.[CH:2]12[NH:11][CH:6]([CH2:7][C:8](=[O:10])[CH2:9]1)[CH2:5][O:4][CH2:3]2.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21](Cl)(=[O:23])=[O:22])([O-:14])=[O:13]>C(Cl)Cl>[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:11]1[CH:6]2[CH2:7][C:8](=[O:10])[CH2:9][CH:2]1[CH2:3][O:4][CH2:5]2)(=[O:23])=[O:22])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 716271383-Oxa-9-azabicyclo[3.3.1]nonan-7-one--hydrogen chloride (1/1)

Product 1

HCID 117697629HCID 117697629, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-oxa-9-azabicyclo[3.3.1]nonan-7-one hydrochloride (CAS 1126795-00-3, 2.82 g), TEA (6.12 g, 60 mmol, 3.0 eq) and 2-Nitro-benzenesulfonyl chloride (8.84 g, 40 mmol, 2.0 eq) in DCM (100 mL) was stirred at room temperature for 10 h. Then the solvent was removed in vacuo, the residue was purified by silica gel (EA/PE=1:3) to give 9-(2-nitrophenyl)sulfonyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-one 107b as a white solid, 4.90 g, yield: 75%. MS: calc'd (MH+) 327, measured (MH+) 327.

Workup

  1. customThen the solvent was removed in vacuo
  2. customthe residue was purified by silica gel (EA/PE=1:3)

Sources & evidence

ORD record
ord-875cb058775548bbb49fcd526d7a6658
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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