1H-1,2,4-Triazole → HCID 59007752, compound

HRID 641086Notes

Reaction equation

HRID 641086 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[C:11]1[C:12]([Cl:19])=[N:13][C:14](Cl)=[CH:15][C:16]=1[Cl:17].[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1.P([O-])(O)(O)=O.[Na+]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[C:11]1[C:12]([Cl:19])=[N:13][C:14]([N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)=[CH:15][C:16]=1[Cl:17]

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 23672064Monosodium phosphateHCID 57430841HCID 57430841, compound

Product 1

HCID 59007752HCID 59007752, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.42 g (11.0 mmol) of 60% sodium hydride in paraffin was added a little at a time to 3.00 g (9.6 mmol) of 3-(2-chloro-6-fluorophenyl)-2,4,6-trichloropyridine and 0.70 g (9.6 mmol) of [1,2,4]triazole dissolved in 30 ml of dimethylformamide. The mixture was stirred at room temperature for 3 d, added to 50 ml of sodium dihydrogenphosphate solution, extracted three times with in each case 50 ml of methyl tert-butyl ether, dried over sodium sulfate and concentrated under reduced pressure. The crude product was chromatographed on silica gel using cyclohexane/ethyl acetate. Yield 1.5 g of a colorless solid of m.p. 210° C.

Workup

  1. extractionextracted three times with in each case 50 ml of methyl tert-butyl ether
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-9ef641533553449093392b6e8d7265c5
Source dataset
uspto-grants-2010_04
Patent number
US07695728B2

Reaction notes

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