N-Iodosuccinimide → HCID 135804109, compound

HRID 2415024Notes

Reaction equation

HRID 2415024 reaction equation
[CH:1]([S:4][C:5]1[NH:10][C:9](=[O:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[N:6]=1)([CH3:3])[CH3:2].[I:16]N1C(=O)CCC1=O>C(#N)C>[I:16][C:8]1[C:9](=[O:11])[NH:10][C:5]([S:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]=1[C:12]([F:14])([F:15])[F:13]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 135561638HCID 135561638, compound

Product 1

HCID 135804109HCID 135804109, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Isopropylthio-6-trifluoromethyl-3H-pyrimidin-4-one (23.3 g) was dissolved in acetonitrile (230 ml) and N-iodosuccinimide (24.2 g) was added at room temperature with stirring. The mixture was refluxed for 2.5 hr and the solvent was removed under reduced pressure. The precipitates were dissolved in ethyl acetate, and then washed with aqueous sodium thiosulfate, water and brine, respectively. The ethyl acetate layer was dried over magnesium sulfite and the solvent was removed under reduced pressure to give 5-iodo-2-isopropylthio-6-trifluoromethyl-3H-pyrimidin-4-one (34.8 g) as pale yellow needles, mp 212-215° C.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hr
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe precipitates were dissolved in ethyl acetate
  4. washwashed with aqueous sodium thiosulfate, water and brine
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulfite
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-091181a3f3a540d4b1318385e59ba461
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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