Lawesson's reagent → HCID 60204552, compound

HRID 2267423Notes

Reaction equation

HRID 2267423 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Cl:23][C:24]1[C:25]([C:32]([NH:34][NH:35][C:36](=O)[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=O)=[N:26][C:27]([S:30][CH3:31])=[N:28][CH:29]=1>N1C=CC=CC=1.O>[CH2:37]([C:36]1[S:10][C:32]([C:25]2[C:24]([Cl:23])=[CH:29][N:28]=[C:27]([S:30][CH3:31])[N:26]=2)=[N:34][N:35]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 175865525-chloro-2-(methylsulfanyl)-N'-(phenylacetyl)pyrimidine-4-carbohydrazide

Product 1

HCID 60204552HCID 60204552, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Lawesson's Reagent (0.487 g (1.2 mmol) and 5-chloro-2-(methylthio)-N′-(2-phenyl-acetyl)pyrimidine-4-carbohydrazide (0.442 g, 1.2 mmol) were dissolved in 8 mL pyridine. This solution was heated to 100° C. for 30 h, giving ˜50% conversion. Upon cooling, the reaction mixture was diluted with excess H2O. The aqueous layer was extracted with EtOAc. The combined organic layers were dried with magnesium sulfate and concentrated under vacuum. Flash chromatography was used to obtain 0.190 g (47% yield) product as a brown solid. MS (M+H)+ 335.

Workup

  1. customgiving ˜50% conversion
  2. temperatureUpon cooling
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried with magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-73c10348770d4e67af2a67a21b197820
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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