Lawesson's reagent → HCID 14836063, compound

HRID 1088546Notes

Reaction equation

HRID 1088546 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Cl:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:38][CH3:39])[C:30]=2[C:34]([F:37])([F:36])[F:35])[C:25]=1[C:40]([N:42]([CH3:48])[CH2:43][C:44]([O:46][CH3:47])=[O:45])=O>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:38][CH3:39])[C:30]=2[C:34]([F:37])([F:36])[F:35])[C:25]=1[C:40](=[S:10])[N:42]([CH3:48])[CH2:43][C:44]([O:46][CH3:47])=[O:45]

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 14836047HCID 14836047, compound

Product 1

HCID 14836063HCID 14836063, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (1.9 g, 0.6 eq) was added to a stirred suspension of N-[[2-chloro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, methyl ester (3.00 g, 7.70 mmole) in toluene (30 mL) at room temperature under nitrogen. The reaction was heated to reflux for 42 hours with more Lawesson's reagent (3.9 g, 1.2 eq) added in three equal portions after 11/4, 171/2 and 231/2 hours. The reaction mixture was cooled to room temperature, filtered, and the filtrate absorbed onto silica gel and flash chromatographed (gradient elution:eluant 60/40, chloroform/petroleum ether →9/1 chloroform/acetonitrile) to provide the desired product as a foamy solid (0.98 g) and recovered starting material (1.23 g). The starting material (1.23 g, 3.08 mmole) was suspended in toluene (~15 mL) and treated with Lawesson's reagent as described above to give additional product (0.351 g, combined yield 43%), m.p. 67°-73° C. (softens at 50° C.).

Workup

  1. temperatureThe reaction was heated
  2. additionadded in three equal portions after 11/4, 171/2 and 231/2 hours
  3. filtrationfiltered
  4. customthe filtrate absorbed onto silica gel and flash
  5. customchromatographed
  6. wash(gradient elution:eluant 60/40, chloroform/petroleum ether →9/1 chloroform/acetonitrile)

Sources & evidence

ORD record
ord-6235a330b96a45feabb0584105664957
Source dataset
uspto-grants-1990_10
Patent number
US04962224

Reaction notes

Loading…