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

HRID 860168

반응식

HRID 860168 반응식
[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

참가 물질

6

반응물 2

HCID 555202N-BenzylidenebenzenesulfonamideHCID 178455850HCID 178455850, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c771d8253824418592d5cc5b45108edf
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153868B2

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