Triethylamine → HCID 18315067, compound

HRID 1421470Notes

Reaction equation

HRID 1421470 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](F)[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[C:4]([F:25])[CH:3]=1.C([N:28](CC)CC)C.C([O-])(=O)C.[NH4+]>O1CCOCC1>[NH2:28][C:6]1[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[C:4]([F:25])[CH:3]=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 22991853HCID 22991853, compound

Product 1

HCID 18315067HCID 18315067, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To stirred solution of 200 grams (0.519 mole) of 3-(4-chloro-2,6-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 1000 mL of dioxane was added 150 mL (1.091 moles) of triethylamine in one portion. Upon completion of addition, the mixture was vigorously stirred and 400 grams (5.189 moles) of ammonium acetate was added in one portion. The reaction mixture was heated to 90° C. where it stirred for two hours. The reaction mixture was allowed to cool to ambient temperature where it stirred for about 18 hours. The resulting suspension was collected by filtration and washed with dioxane. The filtrate was concentrated under reduced pressure to yield a viscous dark oil. The oil was poured into ice-water. The resulting solid was collected by filtration and washed with water. The solid was dried under reduced pressure and then at ambient temperature for about 18 hours, yielding 195.1 grams of title compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. stirringstirred for two hours
  3. temperatureto cool to ambient temperature where it
  4. stirringstirred for about 18 hours
  5. filtrationThe resulting suspension was collected by filtration
  6. washwashed with dioxane
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto yield a viscous dark oil
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with water
  11. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-9174ebc0bff84114a8684d6fd53df6c5
Source dataset
uspto-grants-2000_06
Patent number
US06077812

Reaction notes

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