Lawesson's reagent → HCID 178488795, 화합물

HRID 539550노트

반응식

HRID 539550 반응식
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]1([N:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]3[N:38]=[N:39][NH:40][CH:41]=3)=[C:31]([O:42][CH3:43])[C:30]2=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[C:23]1([N:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]3[N:38]=[N:39][NH:40][CH:41]=3)=[C:31]([O:42][CH3:43])[C:30]2=[S:10])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 178488794HCID 178488794, 화합물

생성물 1

HCID 178488795HCID 178488795, 화합물수율 121.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a stirring solution of Lawesson's reagent (0.075 g, 0.185 mmol) in toluene (10 mL), was added starting material 158a (0.10 g, 0.33 mmol). Reaction mixture was heated to reflux temperature. After overnight reaction, solvent was evaporated under reduced pressure. Crude product was dissolved in small amount of CH2Cl2 to load onto preparative-TLC and eluted with CHCl3:Acetone:EtOH (10:1:0.2) to give pure yellow solid 160 (0.07 g, 68%). 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J=7.4 Hz, 2H), 7.56 (s, 1H), 7.35 (t, J=7.5 Hz, 2H), 7.28 (m, 1H), 6.97 (d, J=6.6 Hz, 1H), 6.62 (d, J=7.8 Hz, 1H), 6.37 (m, 1H), 5.13 (t, J=5.6 Hz, 2H), 5.03 (t, J=5.6 Hz, 2H), 3.86 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 171.92, 158.94, 147.52, 132.68, 129.92, 128.69, 128.14, 125.43, 120.96, 111.72, 110.22, 56.72, 56.63, 46.38. HRMS (EI) calcd for C16H16N4OS [M]+ 312.104. found 312.1039.

후처리

  1. customReaction mixture
  2. temperaturewas heated
  3. temperatureto reflux temperature
  4. customAfter overnight reaction, solvent
  5. customwas evaporated under reduced pressure
  6. dissolutionCrude product was dissolved in small amount of CH2Cl2
  7. washeluted with CHCl3:Acetone:EtOH (10:1:0.2)

출처 및 근거

ORD 기록
ord-76e92d2b3d7c42b18f08457ab56de5e2
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871728B2

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