Lawesson's reagent → HCID 178488795、化合物

HRID 539550ノート

反応式

HRID 539550 の反応式
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

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 178488794HCID 178488794、化合物

生成物 1

HCID 178488795HCID 178488795、化合物収率 121.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-76e92d2b3d7c42b18f08457ab56de5e2
出典データセット
uspto-grants-2014_10
特許番号
US08871728B2

反応ノート

読み込み中…