Water → HCID 20481922, compound

HRID 648369Notes

Reaction equation

HRID 648369 reaction equation
[CH:1]([C:4]1[N:9]=[C:8]([Cl:10])[C:7]([S:11][CH2:12][CH3:13])=[C:6]([Cl:14])[N:5]=1)([CH3:3])[CH3:2].C(OO)(=[O:17])C.[OH2:20]>C(O)(=O)C.C(Cl)Cl>[CH:1]([C:4]1[N:5]=[C:6]([Cl:14])[C:7]([S:11]([CH2:12][CH3:13])(=[O:17])=[O:20])=[C:8]([Cl:10])[N:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6585Peracetic AcidHCID 20481919HCID 20481919, compound

Product 1

HCID 20481922HCID 20481922, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

9.8 g (0.039 mole) of 2-isopropyl-4,6-dichloro-5-ethylthiopyrimidine are dissolved in 50 ml of acetic acid and then 15.2 g (0.08 mole) of peracetic acid are slowly added dropwise to this solution. The exothermic reaction is kept in check by cooling at 40° C. After being stirred for 24 hours at room temperature, the clear solution is diluted with 4 times its volume of water. The precipitate is isolated by filtration and taken up in methylene chloride. The aqueous filtrate is extracted with methylene chloride and the extract is washed with sodium bicarbonate solution until neutral. The combined methylene chloride phases are dried over magnesium sulfate, filtered and concentrated to an oil. The residue (6.3 g) is distilled in a high vacuum in a bulb tube. At an oven temperature of 150° C./3;10-2 mbar, 5.4 g of 2-isopropyl-4,6-dichloro-5-ethylsulfonylpyrimidine distill in the form of a colourless oil.

Workup

  1. customThe exothermic reaction
  2. customThe precipitate is isolated by filtration
  3. extractionThe aqueous filtrate is extracted with methylene chloride
  4. washthe extract is washed with sodium bicarbonate solution until neutral
  5. dry with materialThe combined methylene chloride phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. distillationThe residue (6.3 g) is distilled in a high vacuum in a bulb tube
  9. customtemperature of 150° C.
  10. distillation10-2 mbar, 5.4 g of 2-isopropyl-4,6-dichloro-5-ethylsulfonylpyrimidine distill in the form of a colourless oil

Sources & evidence

ORD record
ord-a94ce9f7f19b4c639c118f43d09b7fbd
Source dataset
uspto-grants-1983_10
Patent number
US04412074

Reaction notes

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