1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamide

HRID 1990061ノート

反応式

HRID 1990061 の反応式
N12CCCN=C1CCCCC2.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])=[CH:15][CH:14]=1.[CH:26]([S:29](Cl)(=[O:31])=[O:30])([CH3:28])[CH3:27]>ClCCl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][S:29]([CH:26]([CH3:28])[CH3:27])(=[O:31])=[O:30])=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 113686332-(4'-Bromophenyl)aniline

生成物 1

HCID 57974945N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamide収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add dropwise 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) drop wise (8.76 mL, 56.92 mmol) to a solution of 4′-bromo-biphenyl-2-ylamine (3.53 g, 14.23 mmol) in dichloromethane (50 ml) at 0° C., followed by drop wise addition of isopropylsulfonyl chloride (3.29 mL, 28.46 mmol) and stir the reaction at room temperature for 24 h. Remove solvent under reduce pressure and purify the residue by silica and eluting with ethyl acetate:hexane 1:4 to ethyl acetate to provide the title compound (4.93 g, 98%): Mass spectrum (m/e): 355 (M+1); 353 (M−1); 1HNMR (CDCl3) δ 1.24 (d, 6H, J=6.7 Hz); 3.28 (sep, 1H, J=6.9 Hz); 6.22 (s, 1H); 7.12-7.41 (m, 5H); 7.55-7.68 (m, 3H).

後処理

  1. customthe reaction at room temperature for 24 h
  2. custompurify the residue by silica
  3. washeluting with ethyl acetate:hexane 1:4 to ethyl acetate

出典と根拠

ORDレコード
ord-fd397fd6ca744f64ace324d2c5163ed7
出典データセット
uspto-grants-2010_01
特許番号
US07642361B2

反応ノート

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