Sodium → HCID 20227479, compound

HRID 1731467Notes

Reaction equation

HRID 1731467 reaction equation
[Na].[Cl:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N:11]2[C:15](=[O:16])[NH:14][C:13](=O)N2)=[C:5]([F:18])[CH:4]=1>CO>[Cl:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N:11]2[C:15](=[O:16])[N:11]3[CH:6]=[CH:5][CH:4]=[CH:3][CH2:13][N:14]3[C:15]2=[O:16])=[C:5]([F:18])[CH:4]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 20227476HCID 20227476, compound

Product 1

HCID 20227479HCID 20227479, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of metallic sodium (0.46 g) in methanol (20 ml), 2-(4-chloro-2-fluoro-5-methoxyphenyl)urazol (2.6 g) was added, and the resultant mixture was concentrated under reduced pressure. The residue was dissolved in dimethylformamide (20 ml), 1,5-dibromopentane (2.3 g) was added thereto, and the resulting mixture was stirred at 100° to 120° C. for 4 hours. After being allowed to cool, water was added to the mixture, which was then extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallized from methanol to give 0.42 g of 2-(4-chloro-2-fluoro-5-methoxyphenyl)-1H,5H-[1,2,4]triazolo[1,2-a][1.2]diazepine-1,3(2H)-dione (Compound No. 3). M.P., 121.5°-123° C. IR νmax (cm-1) 1750, 1680. NMR δ (ppm): 1.8 (6H, m), 3.9 (3H, s).

Workup

  1. concentrationthe resultant mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dimethylformamide (20 ml)
  3. addition1,5-dibromopentane (2.3 g) was added
  4. temperatureto cool
  5. additionwater was added to the mixture, which
  6. extractionwas then extracted with ethyl acetate
  7. washThe extract was washed with a saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-18a9faa33c684bddb3a6dd84982477b2
Source dataset
uspto-grants-1986_11
Patent number
US04622063

Reaction notes

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