Dichloromethane → 8-Bromo-2-chloroquinazoline

HRID 1672469

반응식

HRID 1672469 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 457900618-Bromo-2-chloroquinazoline수율 67.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c761042b62864079a88a12fad225bcfb
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998978B2

연결된 노트

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