Toluene → HCID 21083994, compound

HRID 347936Notes

Reaction equation

HRID 347936 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[C:35](=[O:36])[CH:34]=[CH:33][C:32]2[C:37]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[C:38]([C:40]([NH2:42])=O)[S:39][C:31]1=2.C1(C)C=CC=CC=1>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[C:35](=[O:36])[CH:34]=[CH:33][C:32]2[C:37]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[C:38]([C:40](=[S:10])[NH2:42])[S:39][C:31]1=2

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagent2×HCID 21083995HCID 21083995, compound

Product 1

HCID 21083994HCID 21083994, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of Lawesson's reagent (26.3 mg, 0.065 mmol) and the compound of Example 127 (50 mg, 0.13 mmol) was added toluene (10 mL) and the reaction heated at 110° for 1 h. A further portion of Lawesson's reagent (52.6 mg, 0.13 mmol) was added and reaction heated for 6.5 h. The reaction was diluted with DCM, washed with water, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica, 5–10% EtOAc in DCM) to give the title compound as a yellow solid (10 mg, 20%). δH (MeOH-d4) 7.67 (1H, m), 7.58–7.46 (7H, m), 7.40 (3H, m), 6.48 (1H, d, J 9.6 Hz). LCMS (ES+) RT 3.41 minutes, 397 (M+H)+.

Workup

  1. temperaturethe reaction heated at 110° for 1 h
  2. customreaction
  3. temperatureheated for 6.5 h
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica, 5–10% EtOAc in DCM)

Sources & evidence

ORD record
ord-bb5af583b75a44ac9f9000797a902310
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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