Ethyl Acetate → 2-(1-Bromoethyl)3-(4-fluorophenyl)-3H-quinazolin-4-one

HRID 1827327ノート

反応式

HRID 1827327 の反応式
[CH2:1]([C:3]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:11](=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:26]Br.C(OCC)(=O)C>C(O)(=O)C.CCCCCC.O>[Br:26][CH:1]([C:3]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:11](=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 24408Bromine2 回HCID 517045Sodium AcetateHCID 120180582-Ethyl-3-(4-fluorophenyl)-3H-quinazolin-4-one2 回

生成物 1

HCID 120180572-(1-Bromoethyl)3-(4-fluorophenyl)-3H-quinazolin-4-one収率 96.1%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒HCID 8058Hexane溶媒

反応条件

温度
40 °C

実験手順

To a solution of 7.084 g 2-ethyl-3-(4-fluorophenyl)-3H-quinazoline-4-one (IV) (26.40 mmol, 1.000 equiv) and 2.60 g sodium acetate (31.7 mmol, 1.20 equiv) dissolved in 30 mL glacial acetic acid at 40° C. (external temperature; oil bath) was added dropwise by addition funnel a solution of 1.36 mL bromine (26.4 mmol, 1.00 equiv) in 5 mL glacial acetic acid over 60 min. Upon completed addition of the bromine solution, the reaction was stirred an additional 60 min, after which time TLC indicated no IV remained (Rf=0.44; 40% ethyl acetate in hexane) and the heterogeneous mixture was poured into 400 mL water. The resulting aqueous, acidic mixture, with precipitate, was stirred vigorously at ambient temperature for two h. The precipitate was collected by vacuum filtration, rinsing with warm (ca. 40° C.) water (2×50 mL) and cold isopropyl alcohol (50 mL). The solid was dried in vacuo over phosphorous pentoxide overnight, affording 8.81 g of a white solid.m.p. 179.8° C. 1H NMR (CDCl3) δ 2.06 (d, J=0.016p, 3H), 4.55 (q, 0.016 p, 2H), 7.16 (ddd, 1H, J1=2.4 Hz, J2=4.8 Hz, J3=8.4 Hz), 7.24 (dt, 1H, J1=2.8 Hz, J2=8.0 Hz), 7.28 (dt, 1H, J1=2.8 Hz, J2=8.4 Hz), 7.51–7.58 (m, 2H), 7.80–7.81 (m, 2H), 8.28 (dt, 1H, J1=0.8 Hz, J2=8.0 Hz) ppm. MS (ESI+) 348.0 [MH]+.

後処理

  1. stirringThe resulting aqueous, acidic mixture, with precipitate, was stirred vigorously at ambient temperature for two h
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washrinsing
  4. dry with materialThe solid was dried in vacuo over phosphorous pentoxide overnight

出典と根拠

ORDレコード
ord-f796d6f26f7448b395d2041ff60af79d
出典データセット
uspto-grants-2006_05
特許番号
US07053215B2

反応ノート

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