Lawesson's reagent → HCID 57683205, compound

HRID 2427289Notes

Reaction equation

HRID 2427289 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1([C:24]([NH2:26])=O)[CH2:23][CH2:22]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCCC1.O>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1([C:24](=[S:36])[NH2:26])[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 15980320HCID 15980320, compound

Product 1

HCID 57683205HCID 57683205, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 2 (400 mg, 0.99 mmol) in tetrahydrofuran (32 ml), under nitrogen, was added Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-disulphide, 240 mg, 0.59 mmol). The reaction mixture was heated at reflux for 3 h, cooled to room temperature and diluted with water. The mixture was extracted with ethyl acetate (×3) and the combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in acetonitrile (1.2 ml) and purified by automated preparative liquid chromatography (Gilson system, 150 mm×30 mm Phenomenex LUNA C18(2) 10 μm column) using an acetonitrile:water gradient [45:55 to 95:5]. The appropriate fractions were concentrated in vacuo to give the titled compound (64 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. extractionThe mixture was extracted with ethyl acetate (×3)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in acetonitrile (1.2 ml)
  7. custompurified
  8. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-6f3f09e21b6949ba8372a69dc11dd70e
Source dataset
uspto-grants-2011_06
Patent number
US07968584B2

Reaction notes

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