Lawesson's reagent → 6-bromo-8-chloro-3,4-dihydroquinoline-2(1H)-thione

HRID 1521624

반응식

HRID 1521624 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[NH:8][C:7](=O)[CH2:6][CH2:5]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[NH:8][C:7](=[S:23])[CH2:6][CH2:5]2

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 709797726-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 899616046-bromo-8-chloro-3,4-dihydroquinoline-2(1H)-thione

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 6-bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one (80-1; 10 g, 0.038 mol) in toluene (130 mL) was added Lawesson's reagent (7.7 g, 0.019 mol). Reaction mass was refluxed at 100° C. for 3 h. The reaction mixture was concentrated and directly purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ: 11.25 (s, 1H), 7.61-7.60 (d, J=2.4 Hz, 1H), 7.48 (s, 1H), 2.96-2.93 (m, 2H), 2.85-2.81 (m, 2H). MS (M+2): 277.

후처리

  1. customReaction mass
  2. concentrationThe reaction mixture was concentrated
  3. customdirectly purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-82d59694bcf54d2a820b1e4ff8bb5270
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

연결된 노트

불러오는 중…