Dichloromethane → 8-Bromo-2-chloroquinazoline

HRID 1672469ノート

反応式

HRID 1672469 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 457900618-Bromo-2-chloroquinazoline収率 67.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c761042b62864079a88a12fad225bcfb
出典データセット
uspto-grants-2011_08
特許番号
US07998978B2

反応ノート

読み込み中…