Sodium Sulfate → HCID 59637282, compound

HRID 1843023Notes

Reaction equation

HRID 1843023 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][N:14]2[C:18]([C:19]([NH2:21])=O)=[CH:17][C:16]([C:22]([F:25])([F:24])[F:23])=[N:15]2)=[CH:11][CH:10]=1.C(OCC)(=O)C.CCCCCC.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:18]([CH2:19][NH2:21])=[CH:17][C:16]([C:22]([F:23])([F:24])[F:25])=[N:15]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydride2×HCID 59637298HCID 59637298, compound

Product 1

HCID 59637282HCID 59637282, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LAH (4.7 g, 0.12 mol) was charged into a flask. THF (250 mL) was added at 0° C. Then a solution of 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide (37 g, 0.12 mol) in THF (120 mL) was added drop wise for 30 min at 0° C. and reaction mixture was heated to reflux for 5 h. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.2). As the reaction was not completed, LAH (2.3 g) was added again and the mixture was refluxed for another 4 h. After completion of the reaction, the reaction contents were slowly added to saturated sodium sulfate (1 L) solution and filtered over celite and the product was extracted with ethyl acetate (2×500 mL). The combined extract was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude (1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine as an off white solid (32.5 g, crude). The crude product obtained was directly used for the next step.

Workup

  1. customreaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 5 h
  4. temperaturethe mixture was refluxed for another 4 h
  5. customAfter completion of the reaction
  6. customthe reaction contents
  7. filtrationfiltered over celite
  8. extractionthe product was extracted with ethyl acetate (2×500 mL)
  9. extractionThe combined extract
  10. dry with materialwas dried over sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b7354777c9440ef9f5c7d7c12ade25c
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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