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

HRID 553078노트

반응식

HRID 553078 반응식
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

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9e9bfa9b36994bd8868e0e3740ff0e49
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951827B2

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