Trifluoroacetic acid → HCID 57819988, compound

HRID 1714168Notes

Reaction equation

HRID 1714168 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.FC(F)(F)C(O)=[O:22].[F:26][C:27]([F:37])([F:36])[C:28]1[CH:33]=[CH:32][C:31]([N+:34]#[C-:35])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:35]([NH:34][C:31]2[CH:30]=[CH:29][C:28]([C:27]([F:36])([F:37])[F:26])=[CH:33][CH:32]=2)=[O:22])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 4082852-MorpholinoethylamineHCID 27594124-(Trifluoromethyl)phenyl isocyanide

Product 1

HCID 57819988HCID 57819988, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromobenzaldehyde (3.09 g, 16.7 mmol) in anhydrous MeOH (10 mL) was added N-aminoethyl-morpholine (2.17 g, 16.7 mmol) followed by trifluoroacetic acid (1.90 g, 16.7 mmol) under N2 atmosphere. After stirring the reaction mixture for 5 minutes, 4-trifluoromethylphenylisocyanide (2.85 g, 16.7 mmol) was added and the reaction then heated to 80 degrees Celcius for 2 h. Anhydrous potassium carbonate (4.60 g, 33.3 mmol) was then added and the reaction stirred at 80 degrees Celcius for an additional 2 h. After solvent removal, the residue was diluted with dichloromethane (100 mL) and water (100 mL). The aqueous layer was extracted with dichloromethane (50 mL x2). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with ethyl acetate: petroleum ether gradient (10%-50%) to afford the product as a yellow solid (2.9 g, 35%).

Workup

  1. customthe reaction
  2. temperaturethen heated to 80 degrees Celcius for 2 h
  3. stirringthe reaction stirred at 80 degrees Celcius for an additional 2 h
  4. customAfter solvent removal
  5. additionthe residue was diluted with dichloromethane (100 mL) and water (100 mL)
  6. extractionThe aqueous layer was extracted with dichloromethane (50 mL x2)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash column chromatography
  12. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-dd60a9af5a3e460c900c106dafd64a38
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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