Triethylamine → 1-(5-Acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea

HRID 1480

Reaktionsgleichung

Reaktionsgleichung von HRID 1480
[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[NH:7][C:8](=[O:10])[CH3:9].C(N(CC)CC)C.[C:21]1([O:27]C(Cl)=O)C=CC=CC=1.[CH2:31]([NH2:34])[C:32]#[CH:33]>O1CCCC1.O.C(OCC)(=O)C>[C:8]([NH:7][C:6]1[C:5]([F:12])=[CH:4][C:3]([Cl:13])=[C:2]([NH:1][C:21]([NH:34][CH2:31][C:32]#[CH:33])=[O:27])[CH:11]=1)(=[O:10])[CH3:9]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 239041PropargylamineHCID 11769584N-(5-amino-4-chloro-2-fluorophenyl)acetamide

Produkt 1

HCID 538737111-(5-Acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5'-amino-4'-chloro-2'-fluoroacetanilide (11.25 g, 55.6 mmol), and triethylamine (7.70 mL, 55.6 mmol) in tetrahydrofuran is added dropwise to a stirred solution of phenylchloroformate (8.70 mL, 69.4 mmol) in tetrahydrofuran while maintaining the reaction mixture temperature at 25°-30° C. After the addition is complete, the reaction mixture is stirred at room temperature for 75 minutes, and poured into ethyl acetate. The organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a tan solid. A solution of the solid in tetrahydrofuran is treated with propargylamine (9.52 mL, 139 mmol), refluxed for 1 hour, and poured into water. The aqueous mixture is filtered to obtain a solid which is washed sequentially with water, 0.5N hydrochloric acid and water, and dried overnight to give the title product as a beige solid.

Aufarbeitung

  1. temperaturewhile maintaining the reaction mixture temperature at 25°-30° C
  2. additionAfter the addition
  3. washThe organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a tan solid
  7. temperaturerefluxed for 1 hour
  8. filtrationThe aqueous mixture is filtered
  9. customto obtain a solid which
  10. washis washed sequentially with water, 0.5N hydrochloric acid and water
  11. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-5a556d937a384abda5eb0822445fcd79
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726126

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