Iodine → HCID 70099609, compound

HRID 1274620Notes

Reaction equation

HRID 1274620 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([C:10]2[C:14]3[CH:15]=[C:16]([N:19]4[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]4=[O:31])[CH:17]=[CH:18][C:13]=3[S:12][N:11]=2)[CH:4]=1.[I:32]I>C(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[I:32][C:6]1[C:5]([C:10]2[C:14]3[CH:15]=[C:16]([N:19]4[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]4=[O:31])[CH:17]=[CH:18][C:13]=3[S:12][N:11]=2)=[CH:4][C:3]([O:2][CH3:1])=[C:8]([CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 70097426HCID 70097426, compound

Product 1

HCID 70099609HCID 70099609, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-[3-(6-methoxy-p-tolyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.34 g, 0.00300 mol), silver trifluoroacetate and methylene chloride is treated with iodine (1.14 g, 0.00450 mol) in portions, stirred overnight at room temperature, diluted with methylene chloride, washed with 1M sodium thiosulfate and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to a brown oil which solidifies on standing. Recrystallization from ether affords the title compound as a light yellow crystalline solid (1.50 g, 87.2%, mp 210-212° C.).

Workup

  1. washwashed with 1M sodium thiosulfate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo to a brown oil which
  4. customRecrystallization from ether

Sources & evidence

ORD record
ord-0a84eb26cb064762a875f20480e67e3a
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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