Lawesson's reagent → HCID 10466418, compound

HRID 1825850Notes

Reaction equation

HRID 1825850 reaction equation
[CH3:1][CH2:2][CH:3]1[S:8][C:7]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[NH:6][C:4]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C(#N)C>[CH2:2]([CH:3]1[C:4](=[S:24])[NH:6][C:7]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[S:8]1)[CH3:1]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 11528611HCID 11528611, compound

Product 1

HCID 10466418HCID 10466418, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of AF267 (214 mg, 1 mmol) and Lawesson's Reagent (280 mg, 0.692 mmol) in acetonitrile (5 ml) was heated under reflux for 17 hrs. The solvent was removed and residue was dissolved in concentrate aqueous sodium carbonate (0.5 ml) and then extracted with ethyl acetate. The extract was dried and the solvent evaporated. The residue (250 mg), recrystallized first from toluene and then from acetonitrile gave pure AF510. 1H-NMR (CDCl3) δ 1.03 (t, CH3CH2), 1.83 (m), 1.93–2.44 (m), 2.30 (s, CH3N), 2.80 (m, 2H), 4.21 (dd, SCH), 8.66 (br, NH) ppm. MS m/e 230 (M30), 197 (M+−SH), 156, 128, 96 (100%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hrs
  3. customThe solvent was removed
  4. dissolutionresidue was dissolved in concentrate aqueous sodium carbonate (0.5 ml)
  5. extractionextracted with ethyl acetate
  6. customThe extract was dried
  7. customthe solvent evaporated
  8. customThe residue (250 mg), recrystallized first from toluene
  9. customfrom acetonitrile gave pure AF510

Sources & evidence

ORD record
ord-d649a37378234ea183ec6d76a17e7d3d
Source dataset
uspto-grants-2006_05
Patent number
US07049321B2

Reaction notes

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