Dichloromethane → 8-Bromo-2-chloroquinazoline

HRID 1672469

Reaktionsgleichung

Reaktionsgleichung von HRID 1672469
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[N:8]=[C:7]2N.N(OCCC(C)C)=O.CC(=O)OCC.C(Cl)Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[N:8]=[CH:7]2

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8053Isoamyl NitriteHCID 8857Ethyl AcetateHCID 137858778-Bromo-2-chloroquinazolin-4-amine

Produkt 1

HCID 457900618-Bromo-2-chloroquinazolineAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred mixture of 8-bromo-2-chloroquinazolin-4-amine (12.93 g, 50 mmol) in THF (500 mL) was added isoamyl nitrite (23.43 g, 200 mmol) over 3 hours and 40 mins at 60° C. The mixture was stirred for another 5 hours. TLC (PE:EA, 1:1) showed reaction complete. After cooling to room temperature, the solvent was stripped and the residue was taken into DCM (300 mL). The organic layer was washed with brine (100 mL), water (100 mL), then dried over anhydrous Na2SO4 and purified by chromatography (DCM:PE, 1:1) to give the title compound as a yellow solid (8.21 g, 67%). 1HNMR (DMSO-d6, 400 MHz): δ 9.66 (s, 1H), 8.45 (dd, J=0.8, 7.6 Hz, 1H), 8.26 (dd, J=0.8, 8.0 Hz, 7.73 (dd, J=7.6, 8.0 Hz, 1H).

Aufarbeitung

  1. custom40 mins
  2. customat 60° C
  3. customreaction complete
  4. washThe organic layer was washed with brine (100 mL), water (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. custompurified by chromatography (DCM:PE, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c761042b62864079a88a12fad225bcfb
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998978B2

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