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

HRID 553078Notes

Reaction equation

HRID 553078 reaction equation
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

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-9e9bfa9b36994bd8868e0e3740ff0e49
Source dataset
uspto-grants-2011_05
Patent number
US07951827B2

Reaction notes

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