HCID 178433549, compound → HCID 178433210, compound

HRID 491273Notes

Reaction equation

HRID 491273 reaction equation
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([CH3:11])[N:5]=[C:4](S)[N:3]=1>OO>[OH:1][C:2]1[C:7]([CH:8]([CH3:9])[CH3:10])=[C:6]([CH3:11])[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 178433549HCID 178433549, compound

Product 1

HCID 178433210HCID 178433210, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Conditions

Temperature
72.5 °C

Procedure

550 ml of 12 percent hydrogen peroxide solution was heated to 60° C. 4-Hydroxy-5-isopropyl-6-methylpyrimidine-2-thiol (50 g, 0.27 mole) was added in portions. The temperature was maintained at 70-75° C. by rate of addition and application of external heat. 20 min. after completion of the addition approx. 150 ml of distillate was removed under vacuum. The pH was adjusted to 7-8 by addition of 50 percent NaOH solution and the solution of was saturated with solid NaCl. The precipitated product was taken up in 150 ml dichloromethane. The inorganic solids were removed from the aqueous phase by filtration and the filtrate was extracted with dichloromethane (4×50 mL). The combined extracts were dried over sodium sulfate and evaporated to yield 15.6 g (38 percent yield).

Workup

  1. addition20 min. after completion of the addition approx. 150 ml of distillate
  2. customwas removed under vacuum
  3. additionThe pH was adjusted to 7-8 by addition of 50 percent NaOH solution
  4. customThe inorganic solids were removed from the aqueous phase by filtration
  5. extractionthe filtrate was extracted with dichloromethane (4×50 mL)
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. customevaporated
  8. customto yield 15.6 g (38 percent yield)

Sources & evidence

ORD record
ord-cdeab95221394f66b58316dbbb31a3a6
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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