Lawesson's reagent → HCID 86622487, compound

HRID 606936Notes

Reaction equation

HRID 606936 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]1([C:29]#[C:30][C:31]2[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=2)[C:36]([NH2:38])=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[C:23]1([C:29]#[C:30][C:31]2[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=2)[C:36]([NH2:38])=[S:10])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 17975300HCID 17975300, compound

Product 1

HCID 86622487HCID 86622487, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add Lawesson's Reagent, [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphate -2,4-disulfide], (0.42 g, 1.03 mmol) to a suspension of 5-phenylethynyl-nicotinamide (0.12 g, 0.52 mmol) in toluene (3 mL) and stir for 48 h. Concentrate the reaction mixture and purify the residue by silica gel chromatography, eluting with 10:90 to 60:40 with ethyl acetate:hexanes, to give the title compound as a pale yellow solid (0.05 g, 40%).

Workup

  1. concentrationConcentrate the reaction mixture
  2. custompurify the residue by silica gel chromatography
  3. washeluting with 10:90 to 60:40 with ethyl acetate

Sources & evidence

ORD record
ord-e4252d786564422aa28392b276201679
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

Loading…