Lawesson's reagent → HCID 68911731, compound

HRID 1455282Notes

Reaction equation

HRID 1455282 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([NH:26][NH:27][C:28](=O)[CH2:29][N:30]1[C:34]([CH2:35][CH3:36])=[C:33]([O:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=2)[C:32]([CH2:46][CH3:47])=[N:31]1)(=O)[CH3:24]>O1CCCC1>[CH2:46]([C:32]1[C:33]([O:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=2)=[C:34]([CH2:35][CH3:36])[N:30]([CH2:29][C:28]2[S:10][C:23]([CH3:24])=[N:26][N:27]=2)[N:31]=1)[CH3:47]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68955800HCID 68955800, compound

Product 1

HCID 68911731HCID 68911731, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lawesson's reagent (213 mg, 0.53 mmol) was added to a solution of the acetyl acetohydrazide of step (b) of Example 140 (170 mg, 0.48 mmol) in tetrahydrofuran (10 ml) and the reaction mixture was stirred at room temperature for 18 hours. It was then evaporated to dryness and purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (1:1 then 2:1, by volume) to provide the title compound (80 mg, 47%).

Workup

  1. customIt was then evaporated to dryness
  2. custompurified by flash chromatography on silica gel eluting with ethyl acetate:pentane (1:1

Sources & evidence

ORD record
ord-4c241ee4fbe34fabbd0f57fed809fa7b
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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