Dimethyl Sulfate → 3-(2,3-Dichloro-5-nitrophenylmethyl)-1-methyl-6-trifluoromethyluracil

HRID 2292467Notes

Reaction equation

HRID 2292467 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[NH:15][C:14]1=[O:24].S(OC)(O[CH3:29])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:29])[C:14]1=[O:24]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 214781043-(2,3-Dichloro-5-nitrophenylmethyl)-6-trifluoromethyluracil

Product 1

HCID 214781273-(2,3-Dichloro-5-nitrophenylmethyl)-1-methyl-6-trifluoromethyluracilYield 20.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

By the method of Example 1, Step H, 24.5 grams (0.064 mole) of 3-(2,3-dichloro-5-nitrophenylmethyl)-6-trifluoromethyluracil, 12.07 grams (0.096 mole) of dimethyl sulfate, and 17.64 grams (0.127 mole) of potassium carbonate were reacted in 300 mL of acetone, yielding 5.30 grams of 3-(2,3-dichloro-5-nitrophenylmethyl)-1-methyl-6-trifluoromethyluracil as a bright yellow solid. The NMR spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-fe5b77b95182491a9ee77c7c9c7deb8d
Source dataset
uspto-grants-1997_11
Patent number
US05683966

Reaction notes

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