N-Benzylidenebenzenesulfonamide → N-(1-phenylbut-3-enyl)benzenesulfonamide

HRID 860168

Reaction equation

HRID 860168 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH:6](=[N:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC.C1COCC1.[Cl-].[Na+].O>[C:7]1([CH:6]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:16])[CH2:3][CH:2]=[CH2:1])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 555202N-BenzylidenebenzenesulfonamideHCID 178455850HCID 178455850, compound

Product 1

HCID 10946112N-(1-phenylbut-3-enyl)benzenesulfonamideYield 65%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of allyl magnesium bromide (12 mmol) in Et2O (1.0 M, 12 mL) was added dropwise over 10 min to a stirred solution of N-benzylidenebenzene sulfonamide (2.5 g, 10.2 mmol) in THF (40 mL) under N2. After 2 h the mixture was poured into brine and extracted with EtOAc. These extracts were washed with H2O and brine then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with CH2Cl2 to give the benzenesulfonamide as a white solid (1.9 g, 65%). 1H NMR (360 MHz, CDCl3) δ 2.44–2.48 (2H, m), 4.39–4.45 (11H, m), 4.79 (11H, d, J=5.6 Hz), 5.04–5.10 (2H, m), 5.46–5.58 (1H, m), 7.04–7.07 (2H, m), 7.15–7.19 (3H, m), 7.32–7.37 (2H, m), 7.43–7.48 (1H, m), 7.64–7.67 (2H, m).

Workup

  1. extractionextracted with EtOAc
  2. washThese extracts were washed with H2O and brine
  3. dry with materialthen dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with CH2Cl2

Sources & evidence

ORD record
ord-c771d8253824418592d5cc5b45108edf
Source dataset
uspto-grants-2006_12
Patent number
US07153868B2

Linked notes

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