Lawesson's reagent → HCID 178488795, compound

HRID 539550Notes

Reaction equation

HRID 539550 reaction equation
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

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 178488794HCID 178488794, compound

Product 1

HCID 178488795HCID 178488795, compoundYield 121.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-76e92d2b3d7c42b18f08457ab56de5e2
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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