Chloroform → 3-(5-Cyano-2-nitrophenyl)-5-(3-cyanophenyl)isoxazole

HRID 553078ノート

反応式

HRID 553078 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-:22])=[O:21])=[C:6]([C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=3)[O:10][N:9]=2)[CH:7]=1.[CH:23]([Cl:26])(Cl)Cl.Br[C:28]1[CH:29]=[CH:30][C:31]([O:46][CH3:47])=[C:32]([C:34]2[CH:38]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41](Br)[CH:40]=3)[O:36][N:35]=2)[CH:33]=1.Br[C:49]1[CH:53]=[CH:52][O:51][N:50]=1>C(Cl)Cl>[C:49]([C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-:22])=[O:21])=[C:6]([C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:34]#[N:35])[CH:14]=3)[O:10][N:9]=2)[CH:7]=1)#[N:50].[C:8]([C:28]1[CH:29]=[CH:30][C:31]([O:46][CH3:47])=[C:32]([C:34]2[CH:38]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([C:49]#[N:50])[CH:40]=3)[O:36][N:35]=2)[CH:33]=1)#[N:9].[Cl:26][C:23]1[CH:28]=[CH:33][C:32]([C:34]#[N:35])=[CH:31][C:30]=1[C:49]1[CH:53]=[C:52]([C:3]2[CH:2]=[CH:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=2)[O:51][N:50]=1

参加物

8

反応物 4

HCID 6212ChloroformHCID 139338913-Bromo-1,2-oxazoleHCID 166591733-(5-Bromo-2-nitrophenyl)-5-(3-bromophenyl)isoxazoleHCID 166593443-(5-Bromo-2-methoxyphenyl)-5-(3-bromophenyl)isoxazole

生成物 3

HCID 166592173-(5-Cyano-2-nitrophenyl)-5-(3-cyanophenyl)isoxazoleHCID 166593493-(5-Cyano-2-methoxyphenyl)-5-(3-cyanophenyl)isoxazoleHCID 166594683-(2-Chloro-5-cyanophenyl)-5-(4-cyanophenyl)isoxazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-(5-Cyano-2-nitrophenyl)-5-(3-cyanophenyl)isoxazole (501) was prepared from bromoisoxazole 49j as light yellow crystals (0.18 g, 24%): mp 225-227° C. (CHCl3); 1H NMR δ 8.48 (s, 1H), 8.45 (s, 1H), 8.35 (m, 2H), 8.25 (d, J=7.7 Hz, 1H), 8.05 (d, J=7.7 Hz, 1H), 7.82 (t, J=7.7 Hz, 1H), 7.70 (s, 1H); HPLC (Method B) tR 6.67 min (100 area % at 265 nm). Anal. (C17H8N4O3) C, H, N. 3-(5-Cyano-2-methoxyphenyl)-5-(3-cyanophenyl)isoxazole (50m) was prepared from bromoisoxazole 49k as light yellow crystals (1.41 g, 43%): mp 241-243° C. (CH2Cl2); 1H NMR δ 8.49 (s, 1H), 8.26 (m, 2H), 8.00 (br s, 2H), 7.78 (br s, 1H), 7.68 (br s, 1H), 7.42 (s, 1H); HPLC (Method B) tR 7.36 min (97.8 area % at 265 nm). Anal. (C18H11N3O2) C, H, N. 3-(2-Chloro-5-cyanophenyl)-5-(4-cyanophenyl)isoxazole (53j) was prepared by the general method for nitriles 50 above from bromoisoxazole 53i (1.90 g, 5.28 mmol). The crude product was purified by column chromatography (CHCl3). Purified fractions were evaporated. The residue was suspended in ether and filtered off to give a pale yellow solid (0.44 g, 27%); mp 257-259° C.; 1H NMR δ 8.29 (d, J=2.1 Hz, 1H), 8.17 (d, J=8.4 Hz, 2H), 8.08 (m, 3H), 7.95 (d, J=8.4 Hz, 1H), 7.80 (s, 1H); HPLC (Method B) tR 7.55 min (92.3 area % at 265 nm). Anal. (C17H8ClN3O.0.2H2O) C, H, N.

後処理

  1. customThe crude product was purified by column chromatography (CHCl3)
  2. customPurified fractions were evaporated
  3. filtrationfiltered off

出典と根拠

ORDレコード
ord-9e9bfa9b36994bd8868e0e3740ff0e49
出典データセット
uspto-grants-2011_05
特許番号
US07951827B2

反応ノート

読み込み中…