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

HRID 860168

反応式

HRID 860168 の反応式
[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

参加物

6

反応物 2

HCID 555202N-BenzylidenebenzenesulfonamideHCID 178455850HCID 178455850、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c771d8253824418592d5cc5b45108edf
出典データセット
uspto-grants-2006_12
特許番号
US07153868B2

関連ノート

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