2-Thiophenesulfonamide → HCID 67332485、化合物

HRID 1258376ノート

反応式

HRID 1258376 の反応式
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=O)[CH:4]=[C:3]1[S:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[S:25]([NH2:28])(=[O:27])=[O:26]>Cl[Ti](Cl)(Cl)Cl.C(N(CC)CC)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[N:28][S:25]([C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)(=[O:27])=[O:26])[CH:4]=[C:3]1[S:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

参加物

5

反応物 2

HCID 728812-ThiophenesulfonamideHCID 13813614Ethyl [(1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetate

生成物 1

HCID 67332485HCID 67332485、化合物収率 60.4%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8471Triethylamine溶媒

実験手順

63 mg (0.228 mmoles) ethyl 2-(1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetate (7a) was mixed with 37 mg (0.228 mmoles) thiophene-2-sulfonamide in 2.5 ml dichloromethylene, to which at 0° C. was added 76 mg TiCl4.2THF followed by 70 μl triethylamine. The mixture was heated at 60° C. with microwave synthesizer (Initiator 8, Biotage) for 20 min. Diluted with dichloromethylene to 60 ml, the reaction mixture was washed with H2O and brine and dried over Na2SO4. After removal of Na2SO4, the filtrate was concentrated and the residue was purified with flash column (EtOAc/Hexane) affording title compound 58 mg (60.4%) as orange oil which was solidified on standing, m.p.: 110-112° C.

後処理

  1. additionDiluted with dichloromethylene to 60 ml
  2. washthe reaction mixture was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of Na2SO4
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified with flash column (EtOAc/Hexane)

出典と根拠

ORDレコード
ord-d76036d48da34be1a5b70effc8745b28
出典データセット
uspto-grants-2013_06
特許番号
US08466157B2

反応ノート

読み込み中…