Sodium Thiosulfate → 5-iodo-3,6-dimethyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione

HRID 576737Notes

Reaction equation

HRID 576737 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([CH3:9])[N:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:3]1=[O:20].[I:21]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C.O>[I:21][C:6]1[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:20])[N:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:5]=1[CH3:9]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 867238393,6-dimethyl-1-(3-trifluoromethylphenyl)-pyrimidin-2,4(1H,3H)-dione

Product 1

HCID 867238385-iodo-3,6-dimethyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dioneYield 71%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3,6-dimethyl-1-(3-trifluoromethylphenyl)-pyrimidin-2,4(1H,3H)-dione (prepared in Reference Example 20) (800.0 mg) in acetic acid (13.0 ml) was added in water bath N-iodosuccinimide (784.5 mg) and the resulting mixture was stirred at room temperature for five hours. To the reaction mixture was added water (20 ml) and the resulting mixture was stirred for thirty minutes, and thereto was added sodium thiosulfate solution (20 ml) and the resulting mixture was stirred for thirty minutes. The precipitated solids were collected by filtration and washed with water to afford 5-iodo-3,6-dimethyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (819.3 mg).

Workup

  1. stirringthe resulting mixture was stirred for thirty minutes
  2. stirringthe resulting mixture was stirred for thirty minutes
  3. filtrationThe precipitated solids were collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-e168e9fb80e64b3f845bbf86558420d5
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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