Phosphorus oxybromide → HCID 58432792, compound

HRID 1259316Notes

Reaction equation

HRID 1259316 reaction equation
[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[C:5](=O)[NH:4][CH:3]=1.P(Br)(Br)([Br:22])=O.P(Br)(Br)(Br)=O.C(#N)C.C(=O)(O)[O-].[Na+]>C(#N)C.O.C1(C)C=CC=CC=1>[Br:22][C:5]1[C:6](=[O:18])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:2]([CH3:1])=[CH:3][N:4]=1

Participants

8

Reactant 4

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 59564946HCID 59564946, compoundHCID 131730652HCID 131730652, compound

Product 1

HCID 58432792HCID 58432792, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
25 °C

Procedure

6-Methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyrazine-2,3-dione (289.34 g @ 100%, 1 eq) and toluene (3 L) were charged to a flask and the slurry heated to reflux. Azeotroped water (53 ml) was collected and the slurry cooled to 25° C. The toluene was then removed under reduced pressure at <50° C. to give an off-white powder. This material was then added to acetonitrile (2.95 L) and the reaction mixture heated to 64-67° C. In a separate 2 L 3 necked flask, phosphorus oxybromide (368.4 g, 1.2 eq) was dissolved in acetonitrile (1.475 L). The POBr3/acetonitrile solution was then added to the original flask over 45 minutes at 64-67° C. The reaction mixture was then held at 64-67° C. for 4.5 hours and was then cooled to 20-25° C. Saturated sodium bicarbonate in water (10.3 L) was added over 30 minutes to quench the reaction. The mixture was then stirred for 6 hours at 20-25° C. The solid was then filtered off and the filter-cake washed with water (2×0.55 L) to give the title compound as a water-wet solid (486.4 g, 74.3% @ 100%).

Workup

  1. temperaturethe slurry heated to reflux
  2. customAzeotroped water (53 ml) was collected
  3. customThe toluene was then removed under reduced pressure at <50° C.
  4. customto give an off-white powder
  5. temperaturethe reaction mixture heated to 64-67° C
  6. temperaturewas then cooled to 20-25° C
  7. customto quench
  8. customthe reaction
  9. filtrationThe solid was then filtered off
  10. washthe filter-cake washed with water (2×0.55 L)

Sources & evidence

ORD record
ord-58842c72c74745f2a91d2f2730a9c6df
Source dataset
uspto-grants-2013_06
Patent number
US08466284B2

Reaction notes

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