Lawesson's reagent → (2RS)-1-(Isopropoxycarbonyl)-2-methyl-1,2-dihydro-1,4,5,7-tetraazanaphthalene-3(4H)-thione

HRID 21535Notes

Reaction equation

HRID 21535 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][CH:13]=[N:14][CH:15]=2)[NH:10][C:9](=O)[CH:8]1[CH3:18])=[O:6])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][CH:13]=[N:14][CH:15]=2)[NH:10][C:9](=[S:28])[CH:8]1[CH3:18])=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 19932782HCID 19932782, compound

Product 1

HCID 19932819(2RS)-1-(Isopropoxycarbonyl)-2-methyl-1,2-dihydro-1,4,5,7-tetraazanaphthalene-3(4H)-thioneYield 28%

Procedure

100 mg of (2RS)-1-(isopropoxycarbonyl)-2-methyl-1,2-dihydro-1,4,5,7-tetraazanaphthalen-3(4H)-one from Example 24 were reacted with Lawesson's reagent in analogy to Example 20. The crude product after concentration was chromatographed (silica gel; ethyl acetate/heptane=1:1). 30 mg (28%) of the desired compound, of melting point 203°-204° C., were obtained.

Workup

  1. concentrationThe crude product after concentration
  2. customwas chromatographed (silica gel; ethyl acetate/heptane=1:1)

Sources & evidence

ORD record
ord-cb7cb858867743fd95b620cbded84999
Source dataset
uspto-grants-1995_06
Patent number
US05424311

Reaction notes

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