Hydrochloric Acid → HCID 58155259, compound

HRID 1929489Notes

Reaction equation

HRID 1929489 reaction equation
C(=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:31])=[C:19]([C@@:21]2([CH3:30])[NH:26][C:25](=O)[CH2:24][O:23][C:22]2([CH3:29])[CH3:28])[CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:31])=[C:19]([C@@:21]2([CH3:30])[NH:26][C:25](=[S:41])[CH2:24][O:23][C:22]2([CH3:29])[CH3:28])[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 58155322HCID 58155322, compound

Product 1

HCID 58155259HCID 58155259, compoundYield 289.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

The (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5,6,6-trimethyl-morpholin-3-one (1.13 g; 2.71 mmol) was dissolved in dioxane (80 ml) and the Lawesson's Reagent (691 mg, 1.71 mmol) was added at room temperature. The reaction mixture was stirred at 80° C. for 2 hours. Thereafter, the green solution was cooled to 23° C., then hydrochloric acid (1M, 3.42 ml) was added and the mixture was stirred for 30 minutes at room temperature. For the workup, the reaction mixture was poured into a saturated sodium hydrogen-carbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated at reduced pressure to give blue oil (1.33 g). The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 50/50 as the eluent. The (R)-5-(5-amino-2-fluoro-phenyl)-5,6,6-trimethyl-morpholine-3-thione was obtained as a white foam (0.63 g, 86% of theory). Mass (calculated) C13H17FN2OS [268.354]; (found) [M+H]+=269.

Workup

  1. temperatureThereafter, the green solution was cooled to 23° C.
  2. stirringthe mixture was stirred for 30 minutes at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-0026e8993386484a849ab925a4572826
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

Loading…