Pyridine → N-Benzyl-N-[3-(2-oxo-imidazolidin-1-yl)-phenyl]-benzenesulfonamide

HRID 386472ノート

反応式

HRID 386472 の反応式
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([N:15]2[CH2:19][CH2:18][NH:17][C:16]2=[O:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1>ClCCl>[CH2:1]([N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:19][CH2:18][NH:17][C:16]2=[O:20])[CH:10]=1)[S:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:29])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 436966011-(3-Benzylamino-phenyl)-imidazolidin-2-one

生成物 1

HCID 46182274N-Benzyl-N-[3-(2-oxo-imidazolidin-1-yl)-phenyl]-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 1-(3-benzylamino-phenyl)-imidazolidin-2-one (25 mg, 0.1 mmol), benzenesulphonyl chloride (39 μl, 31 mmol) and pyridine (27 μl, 34 mmol) in dry dichloromethane (1 ml) was heated to reflux for 15 hrs. The reaction mixture was then cooled to room temperature, quenched with water (10 ml) and extracted with dichloromethane (3×7 ml). The organic extracts were combined, dried (magnesium sulphate) and concentrated in vacuo. The crude residue was purified by preparative TLC (eluent 1:1 ethyl acetate:dichloromethane) to afford the title compound as a off white solid (9 mg, 24%). HPLC retention time 8.8 mins. Mass spectrum (ES+) m/z 425 (M+NH4).

後処理

  1. temperatureto reflux for 15 hrs
  2. customquenched with water (10 ml)
  3. extractionextracted with dichloromethane (3×7 ml)
  4. dry with materialdried (magnesium sulphate)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative TLC (eluent 1:1 ethyl acetate:dichloromethane)

出典と根拠

ORDレコード
ord-bd628d5117d048588d53e99d988a9408
出典データセット
uspto-grants-2013_02
特許番号
US08372840B2

反応ノート

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