Triethylamine → HCID 66958646, compound

HRID 1984375Notes

Reaction equation

HRID 1984375 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([C:18]1[N:22]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:21]=[C:20]([C:27]([NH2:29])=O)[CH:19]=1)[CH2:15][CH2:16][CH3:17].C(N(CC)CC)C>ClCCl>[CH2:14]([C:18]1[N:22]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:21]=[C:20]([C:27]#[N:29])[CH:19]=1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 66958386HCID 66958386, compound

Product 1

HCID 66958646HCID 66958646, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluoroacetic anhydride (13.5 mL, 95.4 mmol) in dichloromethane (84 mL) was added over 15 minutes to a 0° C. solution of 5-butyl-1-tert-butyl-1H-pyrazole-3-carboxamide (18.7 g, 86.7 mmol) and triethylamine (36.3 mL, 260 mmol) in dichloromethane (167 mL). The reaction was allowed to stir for 10 minutes before the ice bath was removed. The reaction was stirred at ambient temperature for 1 hour and then 2 M aqueous sodium carbonate was added. The mixture was transferred to a separatory funnel and was extracted with dichloromethane three times. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, eluted with 20% ethyl acetate in hexanes). The appropriate fractions were combined, dried over magnesium sulfate, and concentrated under reduced pressure to yield 11.00 g of 5-butyl-1-tert-butyl-1H-pyrazole-3-carbonitrile as an orange oil.

Workup

  1. customwas removed
  2. addition2 M aqueous sodium carbonate was added
  3. customThe mixture was transferred to a separatory funnel
  4. extractionwas extracted with dichloromethane three times
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, eluted with 20% ethyl acetate in hexanes)
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53fe722b408242c2a0d8cb3a9637e45e
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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