Triethylamine → HCID 67041242, compound

HRID 606115Notes

Reaction equation

HRID 606115 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)=[N:9][OH:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:19]([N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])[CH2:20][C:21]#[CH:22]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:22]=[C:21]([CH2:20][CH2:19][N:23]3[C:27](=[O:28])[C:26]4[C:25](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:24]3=[O:33])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27563164-fluoro-N-hydroxybenzenecarboximidoyl chlorideHCID 11171619N-(3-Butynyl)phthalimide

Product 1

HCID 67041242HCID 67041242, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, 4-fluoro-N-hydroxybenzenecarboximidoyl chloride (31 g, 180 mmol), prepared as described in Parts A through C of Example 11, was added dropwise to a solution of anhydrous triethylamine (19 mL, 210 mmol) and N-(3-butynyl)phthalimide (19.04 g, 95.58 mmol) in dichloromethane (1 L). The reaction was stirred at room temperature for 24 hours and then diluted with dichloromethane, washed sequentially with aqueous potassium carbonate, water, and brine; dried over potassium sulfate; filtered; and concentrated under reduced pressure. The resulting solid was triturated with ethanol, isolated by filtration, and washed with diethyl ether to provide 29.87 g of 2-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-1H-isoindole-1,3(2H)-dione. A portion of the product was recrystallized from isopropyl alcohol and dried to provide an analytically pure sample as white crystals, mp 155.0-156.0° C.

Workup

  1. washwashed sequentially with aqueous potassium carbonate, water, and brine
  2. dry with materialdried over potassium sulfate
  3. filtrationfiltered
  4. concentrationand concentrated under reduced pressure
  5. customThe resulting solid was triturated with ethanol
  6. customisolated by filtration
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-9b4b6ddf6060439bad2c54141091eeb6
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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