Lawesson's reagent → 3-Isobutyl-2,6-dithioxanthine

HRID 883543Notes

Reaction equation

HRID 883543 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[CH:11][NH:10][C:9]=2[C:8](=O)[NH:7][C:6]1=[S:15])[CH:2]([CH3:4])[CH3:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:13]2[N:12]=[CH:11][NH:10][C:9]=2[C:8](=[S:25])[NH:7][C:6]1=[S:15])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 103312193-Isobutyl-2-thioxanthine

Product 1

HCID 117764533-Isobutyl-2,6-dithioxanthineYield 74.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

3-Isobutyl-2-thioxanthine (0.20 g, 0.89 mmol) and Lawesson's reagent (1.1 g, 2.7 mmol) were suspended in toluene (8 mL). This mixture was heated at 120° C. for 17 h. The reaction mixture was cooled and the solvent removed under reduced pressure. 10% Sodium hydroxide (20 mL) was added and the mixture stirred for 10 minutes. This solution was filtered to remove insoluble solids and the solid washed with 10% sodium hydroxide solution. The basic filtrate was treated with dilute acetic acid until pH 4 was reached. The resulting precipitate was collected by filtration and washed with water. Drying of the substance afforded the title compound (0.16 g, 73%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent removed under reduced pressure
  3. addition10% Sodium hydroxide (20 mL) was added
  4. filtrationThis solution was filtered
  5. customto remove insoluble solids
  6. washthe solid washed with 10% sodium hydroxide solution
  7. additionThe basic filtrate was treated with dilute acetic acid until pH 4
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with water
  10. customDrying of the substance

Sources & evidence

ORD record
ord-bbe23b0885a14f41b8a65ba355731d99
Source dataset
uspto-grants-2012_08
Patent number
US08236951B2

Reaction notes

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