Phosphorus oxychloride → 4-Chloropyrrolo(2,1-f)(1,2,4)triazine

HRID 1851095Notes

Reaction equation

HRID 1851095 reaction equation
C(N(C(C)C)CC)(C)C.[CH:10]1[CH:19]=[C:18]2[N:12]([CH:13]=[N:14][NH:15][C:16]2=O)[CH:11]=1.P(Cl)(Cl)([Cl:22])=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH:18]1[CH:19]=[C:10]2[C:11]([Cl:22])=[N:12][CH:13]=[N:14][N:15]2[CH:16]=1

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 32409201H,2H-pyrrolo[1,2-d][1,2,4]triazin-1-one

Product 1

HCID 210816834-Chloropyrrolo(2,1-f)(1,2,4)triazineYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Diisopropylethylamine (3.5 mL, 20.3 mmol) was added to a solution of pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one (2.5 g, 18.5 mmol) dissolved in toluene (37.5 mL) under nitrogen atmosphere. Subsequently, after adding phosphorus oxychloride (5.1 mL, 55.7 mmol), the mixture was heated for 20 hours at 100° C. The resulting reaction mixture was cooled to 0° C. and, after slowly adding sodium bicarbonate aqueous solution, stirred at room temperature for 30 minutes. The resulting aqueous layer was extracted with ethyl acetate, dried with magnesium sulfate, and then filtered. The filtrate was concentrated in vacuum. The resulting yellow solid product was subjected to the next step without purification (2.31 g, 15.0 mmol, 81% yield).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to 0° C.
  3. extractionThe resulting aqueous layer was extracted with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuum
  7. customThe resulting yellow solid product was subjected to the next step without purification (2.31 g, 15.0 mmol, 81% yield)

Sources & evidence

ORD record
ord-aac4df1b1f564c2a90bb7ff55186c652
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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