Hydrochloric Acid → 3-(4-chloro-6-fluoro-3-iodo-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 275660Notes

Reaction equation

HRID 275660 reaction equation
N[C:2]1[C:3]([O:23][CH3:24])=[C:4]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])[C:5]([F:9])=[CH:6][C:7]=1[Cl:8].Cl.N([O-])=O.[Na+].[I-:30].[K+]>>[Cl:8][C:7]1[CH:6]=[C:5]([F:9])[C:4]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])=[C:3]([O:23][CH3:24])[C:2]=1[I:30]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 183150613-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneHCID 23668193Sodium Nitrite

Product 1

HCID 183150713-(4-chloro-6-fluoro-3-iodo-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneYield 57%

Conditions

Temperature
15 °C

Procedure

A solution of 4.0 grams (0.011 mole) of 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione in 25 mL (0.300 mole) of concentrated hydrochloric acid was stirred and cooled in an ice bath. During a 15 minute period, 1.9 grams (0.013 mole) of sodium nitrite was added dropwise at a rate to maintain the reaction temperature at 15° C. Upon completion of addition, the mixture was stirred for 20 minutes and then poured into 15.0 grams (0.090 mole) of potassium iodide. The reaction mixture was stirred for 30 minutes and then filtered. The filter cake was thoroughly washed with distilled water and then taken up in 150 mL of ethyl acetate. The resulting solution was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a brown solid. The solid was subjected to column chromatography on silica gel. Elution was accomplished using 5:1 heptane and ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 3.0 grams of title compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturecooled in an ice bath
  2. additionUpon completion of addition
  3. stirringThe reaction mixture was stirred for 30 minutes
  4. filtrationfiltered
  5. washThe filter cake was thoroughly washed with distilled water
  6. dry with materialThe resulting solution was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto yield a brown solid
  10. washElution
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7dcc6fd1fa8f41a8a9a591c995e5b8ba
Source dataset
uspto-grants-2002_03
Patent number
US06352958B1

Reaction notes

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