Lawesson's reagent → 4-isopropoxycarbonyl-3-(R,S)-phenyl-3,4-dihydro-1,4,5-triazanaphthalene-2(1H)-thione

HRID 21538Notes

Reaction equation

HRID 21538 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[NH:10][C:9](=O)[CH:8]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:6])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[NH:10][C:9](=[S:33])[CH:8]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 199328854-isopropoxycarbonyl-3-(R,S)-phenyl-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-one

Product 1

HCID 199327814-isopropoxycarbonyl-3-(R,S)-phenyl-3,4-dihydro-1,4,5-triazanaphthalene-2(1H)-thioneYield 62%

Procedure

200 mg (0.64 mmol) of 4-isopropoxycarbonyl-3-(R,S)-phenyl-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-one were reacted with 400 mg of Lawesson's reagent in analogy to Example 20 (reaction conditions: 10 hours at 80° C. The crude product was concentrated and chromatographed on silica gel (ethyl acetate/n-heptane=1:2). 130 mg (62%) of 4-isopropoxycarbonyl-3-(R,S)-phenyl-3,4-dihydro-1,4,5-triazanaphthalene-2(1H)-thione, of melting point 188°-189° C., were obtained.

Workup

  1. customreaction conditions
  2. custom10 hours
  3. customat 80° C
  4. concentrationThe crude product was concentrated
  5. customchromatographed on silica gel (ethyl acetate/n-heptane=1:2)

Sources & evidence

ORD record
ord-b78b24c5151147d8a06296c48fd132f4
Source dataset
uspto-grants-1995_06
Patent number
US05424311

Reaction notes

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