Carbon tetrabromide → 2-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one

HRID 591768노트

반응식

HRID 591768 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:24])[NH:5][C:6]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([O:19][CH2:20][CH2:21]O)=[C:14]([CH3:23])[CH:13]=1)=[N:7]2.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[Br:26][CH2:21][CH2:20][O:19][C:15]1[C:16]([CH3:18])=[CH:17][C:12]([C:6]2[NH:5][C:4](=[O:24])[C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[Cl:1])[N:7]=2)=[CH:13][C:14]=1[CH3:23]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1361833855-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

생성물 1

HCID 1364150762-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one수율 88.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one (0.40 g, 1.16 mmol) in anhydrous DMF (10 mL) was added carbon tetrabromide (0.42 g, 1.27 mmol) and triphenylphosphine (0.33 g, 1.27 mmol). The reaction mixture was stirred at room temperature for 27 hours. Solvent was evaporated to dryness in vacuo and the residue triturated with Et2O (15 mL)/EtOAc (15 mL) to give 2-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one (0.42 g). It was used without further purification. The 1H NMR indicated a purity of about 45%.

후처리

  1. customSolvent was evaporated to dryness in vacuo
  2. customthe residue triturated with Et2O (15 mL)/EtOAc (15 mL)

출처 및 근거

ORD 기록
ord-ea6f020bd720458293f4903fe42d477f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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