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

HRID 386472노트

반응식

HRID 386472 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bd628d5117d048588d53e99d988a9408
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372840B2

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