Lawesson's reagent → HCID 86643630, compound
Reaction equation
[Br:1][C:2]1[C:3]([C:16](=O)[NH2:17])=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>O1CCCC1>[Br:1][C:2]1[C:3]([C:16](=[S:28])[NH2:17])=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The crude tert-butyl 5-bromo-4-carbamoylpyridin-2-ylcarbamate (Intermediate 84, 232 mmol) was treated with Lawesson's Reagent (94 g, 232 mmol, 1 eq) and tetrahydrofuran (700 mL), the resulting mixture was heated at reflux for 1 h, then it was allowed to stir at room temperature over the weekend. The mixture was concentrated to dryness in vacuo and toluene (˜300 mL) was added. A bright yellow solid precipitated formed which was collected by filtration and washed with toluene, then dried in the vacuum oven at 50° C. for 4 h, yielding 75 g of a bright yellow solid (97%).