Lawesson's reagent → N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine, Methyl Ester

HRID 1088544Notes

Reaction equation

HRID 1088544 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][O:24][C:25]1[C:26]([C:50]([F:53])([F:52])[F:51])=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([C:35]([N:37]([CH3:43])[CH2:38][C:39]([O:41][CH3:42])=[O:40])=O)=[C:30]([O:44][CH2:45][C:46]([F:49])([F:48])[F:47])[CH:29]=[CH:28]2>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:23][O:24][C:25]1[C:26]([C:50]([F:53])([F:52])[F:51])=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([C:35](=[S:10])[N:37]([CH3:43])[CH2:38][C:39]([O:41][CH3:42])=[O:40])=[C:30]([O:44][CH2:45][C:46]([F:49])([F:48])[F:47])[CH:29]=[CH:28]2

Participants

5

Reactant 2

HCID 87949Lawesson's reagent2×HCID 14836049N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, Methyl Ester

Product 1

HCID 14836054N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine, Methyl EsterYield 64%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Lawesson's reagent (3.20 g, 0.6 eq) was added to a stirred solution of N-[[6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, methyl ester, prepared by the process of Example 3, Step 1 (6.00 g, 13.2 mmol) in toluene (60 mL) at room temperature under argon. The reaction was heated to reflux for 111/2 hours, with more Lawesson's reagent (4.8 g, 0.9 eq) added in two portions after 21/4 and 83/4 hours. The reaction was cooled to room temperature and diluted with methylene chloride (300 mL). The crude reaction mixture was preabsorbed onto silica gel and flash chromatographed (petroleum ether→7:3 petroleum ether:ethyl acetate eluent gradient, silica) to provide the product as a yellow foam (3.94 g, 64%). A small sample was washed with petroleum. The filtrate was evaporated to dryness to provide a yellow solid for analysis, m.p. 104°-105° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 111/2 hours
  3. customThe crude reaction mixture
  4. customwas preabsorbed onto silica gel and flash
  5. customchromatographed (petroleum ether→7:3 petroleum ether:ethyl acetate eluent gradient, silica)

Sources & evidence

ORD record
ord-36ac38f3b62041e5906695abfad4e662
Source dataset
uspto-grants-1990_10
Patent number
US04962224

Reaction notes

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