Lawesson's reagent → HCID 45256600, compound

HRID 1875858Notes

Reaction equation

HRID 1875858 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][NH:24][C:25](=O)[C:26]([CH3:29])([CH3:28])[CH3:27])=O)[C:9]=2[S:31][CH3:32])=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1COCC1>[C:26]([C:25]1[S:42][C:21]([C:10]2[C:9]([S:31][CH3:32])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=2)=[N:23][N:24]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67320835HCID 67320835, compound

Product 1

HCID 45256600HCID 45256600, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hydrazide (9) (70 mg, 0.136 mmol) and Lawesson's reagent (137 mg, 0.339 mmol) in THF (5 mL) was irradiated in a microwave reactor (Biotage Initiator™) for 50 minutes at 155° C. The organic extract was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was subjected to silica gel column chromatography (eluent: hexane/EtOAc=4/1) to obtain 54 mg (78%) of the title compound as a solid.

Workup

  1. extractionThe organic extract
  2. dry with materialwas dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12d8ed2423a1475f8477219956f8fa92
Source dataset
uspto-grants-2012_11
Patent number
US08309584B2

Reaction notes

Loading…