Dicyclohexylcarbodiimide → Pent-4-ynoic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester

HRID 1425669

Reaktionsgleichung

Reaktionsgleichung von HRID 1425669
[C:1]([OH:7])(=[O:6])[C:2]#[C:3][CH2:4][CH3:5].C1(N=C=NC2CCCCC2)CCCCC1.O[N:24]1[C:29](=[O:30])[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]=[N:25]1>C1COCC1>[O:30]=[C:29]1[N:24]([O:6][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[N:25]=[N:26][C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]1=2

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-one2×HCID 3243792-Pentynoic acid

Produkt 1

HCID 59336624Pent-4-ynoic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Pentynoic acid (200 mg, 2.04 mmol) was dissolved in THF (4 mL). The solution was cooled in a brine-icewater bath. A solution of dicyclohexylcarbodiimide (421 mg, 2.04 mmol) in THF (2 mL) was added. 3-Hydroxy-1,2,3-benzotriazin-4(3H)-one (333 mg, 2.04 mmol) was added after 5 minutes. The reaction mixture was stirred 1 h at −10° C. and then 2 h at room temperature. TLC indicated full conversion of 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (eluent: ethyl acetate). Precipitated salts were filtered off. The filtrate was concentrated in vacuo and crystallized from hexane (4 mL). The crystals were filtered off and dried. Yield: 450 mg, 93%. RF=0.8 (ethyl acetate).

Aufarbeitung

  1. temperatureThe solution was cooled in a brine-icewater bath
  2. custom2 h
  3. customat room temperature
  4. filtrationPrecipitated salts were filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customcrystallized from hexane (4 mL)
  7. filtrationThe crystals were filtered off
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b4512c63238b41e6808a75cbeb137263
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08932992B2

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