Nitrogen → HCID 59637290, compound

HRID 1843021Notes

Reaction equation

HRID 1843021 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.N#N.[O:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1)[CH3:13].C(OCC)(=O)C.CCCCCC>CN(C=O)C>[CH3:13][O:12][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:5]2[CH:6]=[CH:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 699934-Methyloxybenzyl chlorideHCID 18070343-(Trifluoromethyl)pyrazoleHCID 21226206Ethyl acetate hexane

Product 1

HCID 59637290HCID 59637290, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (33.08 g (19.85 mol, 60%) was washed with n-hexane, then dry DMF (500 mL) was added drop wise under N2 atmosphere and the mixture was stirred well. A solution of 3-(trifluoromethyl)-1H-pyrazole (75 g, 0.55 mol) in DMF (125 mL) was added drop wise under N2 atmosphere. Then a solution of 4-methoxylbenzyl chloride (86.3 g, 0.55 mol) in DMF (125 mL) was added drop wise and the overall reaction mixture was allowed to stir for 12 h at room temperature. Progress of the reaction was monitored by TLC (10% ethyl acetate/hexane, Rf˜0.4). On completion of the reaction, the reaction contents were poured into ice water (500 mL) and the product was extracted with ethyl acetate (2×400 mL). The ethyl acetate layer was washed with 2N HCl (2×200 ml). Then the contents were dried over sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by CC with 10% ethyl acetate/n-hexane to yield 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole as a brown colored liquid (98 g, 70%).

Workup

  1. washNaH (33.08 g (19.85 mol, 60%) was washed with n-hexane
  2. additiondry DMF (500 mL) was added drop wise under N2 atmosphere
  3. stirringto stir for 12 h at room temperature
  4. customOn completion of the reaction
  5. customthe reaction contents
  6. extractionthe product was extracted with ethyl acetate (2×400 mL)
  7. washThe ethyl acetate layer was washed with 2N HCl (2×200 ml)
  8. dry with materialThen the contents were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by CC with 10% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-707c824126de4a7c8e11d98ca1b05d99
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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