Triethylamine → HCID 57820042, compound

HRID 1714162Notes

Reaction equation

HRID 1714162 reaction equation
[C:1]([O:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[F:22][C:23]([F:32])([F:31])[C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.C(N(CC)CC)C>ClCCl>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH:5]([O:4][C:1](=[O:3])[CH3:2])[C:6](=[O:8])[NH:28][C:27]2[CH:29]=[CH:30][C:24]([C:23]([F:22])([F:31])[F:32])=[CH:25][CH:26]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 65578Oxalyl chlorideHCID 57820057Acetoxy-(4-bromo-phenyl)-acetic acid

Product 1

HCID 57820042HCID 57820042, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cooled solution (0 degrees Celcius) of acetoxy-(4-bromo-phenyl)-acetic acid (6.1 g, 22 mmol) in dichloromethane (30 mL) was added oxalyl chloride (4.2 g, 33 mmol) dropwise. After stirring for an additional 1 hour at room temperature, the reaction mixture was concentrated in vacuo and dried under vacuum. The acid chloride intermediate was dissolved in dichloromethane (20 mL) and then added over 1 hr to a solution of 4-trifluoromethylaniline (4.0 g, 25 mmol) and triethylamine (3.6 mL, 25 mmol) in dichloromethane (10 mL) at 0 degrees Celcius. The reaction was then allowed to warm to room temperature and stirred for 30 minutes. The reaction was diluted with dichloromethane and then washed twice with 1N HCl, twice with saturated sodium bicarbonate, and twice with brine. The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo to furnish a yellow solid. The solid was washed with ether to obtain a white solid (5.7 g, 61%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customdried under vacuum
  3. dissolutionThe acid chloride intermediate was dissolved in dichloromethane (20 mL)
  4. temperatureto warm to room temperature
  5. stirringstirred for 30 minutes
  6. washwashed twice with 1N HCl, twice with saturated sodium bicarbonate
  7. dry with materialThe organic layer was then dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto furnish a yellow solid
  11. washThe solid was washed with ether

Sources & evidence

ORD record
ord-e38a67b37ead4baabeb9b6de9bb277b5
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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