Iodine → 3-(2,3-Dichloro-5-iodophenylmethyl)-1-methyl-6-trifluoromethyluracil

HRID 2292469Notes

Reaction equation

HRID 2292469 reaction equation
N[C:2]1[CH:3]=[C:4]([Cl:23])[C:5]([Cl:22])=[C:6]([CH2:8][N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])[CH:7]=1.[I:24]I.N(OC(C)(C)C)=O>CS(C)=O>[Cl:22][C:5]1[C:4]([Cl:23])=[CH:3][C:2]([I:24])=[CH:7][C:6]=1[CH2:8][N:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]1=[O:21]

Participants

5

Reactant 3

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 214781223-(5-Amino-2,3-dichlorophenylmethyl)-1-methyl-6-trifluoromethyluracil

Product 1

HCID 214781263-(2,3-Dichloro-5-iodophenylmethyl)-1-methyl-6-trifluoromethyluracilYield 110.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

By the method of Example 2, Step B, 2.67 grams (0.00725 mole) of 3-(5-amino-2,3-dichlorophenylmethyl)-1-methyl-6-trifluoromethyluracil, 1.84 grams (0.00725 mole) of iodine, and 1.12 grams (0.0109 mole) of tertiary-butyl nitrite were reacted in 10 mL of dimethyl sulfoxide, yielding 3.83 grams of 3-(2,3-dichloro-5-iodophenylmethyl)-1-methyl-6-trifluoromethyluracil as a light brown solid, m.p. 142°-144° C. The NMR and IR spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-5db35651f0ff43c7995a482f2b1aa516
Source dataset
uspto-grants-1997_11
Patent number
US05683966

Reaction notes

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