Lawesson's reagent → HCID 121317095, compound

HRID 527331Notes

Reaction equation

HRID 527331 reaction equation
[F:1][CH:2]([F:22])[C@:3]1([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[F:21])[NH:8][C:7](=O)[CH2:6][CH2:5][C:4]1([F:11])[F:10].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1(C)C=CC=CC=1>[F:1][CH:2]([F:22])[C@:3]1([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[F:21])[NH:8][C:7](=[S:32])[CH2:6][CH2:5][C:4]1([F:11])[F:10]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 121317102HCID 121317102, compound

Product 1

HCID 121317095HCID 121317095, compoundYield 172.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-6-(difluoromethyl)-5,5-difluoro-6-(2-fluoro-5-nitrophenyl)piperidin-2-one (1.00 g, 3.08 mmol) in toluene (5 mL) was added Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithia-diphosphetane-2,4-disulfide) (686 mg, 1.70 mmol). The mixture was stirred at 100° C. for 2 hours. TLC analysis showed no starting material remained. The mixture was concentrated and the crude product was purified by flash chromatography on silica gel (petroleum ether:ethyl acetate=5:1) to give (S)-6-(difluoromethyl)-5,5-difluoro-6-(2-fluoro-5-nitrophenyl)piperidine-2-thione (1.00 g, 2.94 mmol, 95.4% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude product was purified by flash chromatography on silica gel (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-bd87ac3223854ba6a9fe756cfe93b902
Source dataset
uspto-grants-2016_05
Patent number
US09346797B1

Reaction notes

Loading…