Triethylamine → 2-Amino-1-benzylideneamino-4-(4-biphenylyl)-imidazole

HRID 357613Notes

Reaction equation

C(N(CC)CC)C.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=O.[C:24]([NH:27][N:28]=[CH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[NH:26])[NH2:25]>C(O)C>[NH2:26][C:24]1[N:27]([N:28]=[CH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[N:25]=1

Participants

Conditions

Temperature: 20 °C

Procedure

7 ml (0.0507 mol) of triethylamine and 13.75 g (0.050 mol) of 2-bromo-4'-phenylaceto-phenone (Aldrich, Buchs, Switzerland; tech., Cat. no. 10,108-7) are added to a solution of 8.11 g (0.05 mol) of benzaldehyde guanylhydrazone in 40 ml of ethanol. The reaction mixture is stirred at 20° C. for 15 hours and is filtered, and the crystallizate is taken up in methylene chloride and acidified to pH 1 with 1N hydrochloric acid. After filtration, the filtration product is taken up in methanol, and 2N sodium hydroxide solution is added until a basic reaction is obtained (pH 11). Filtration is carried out and the crystalline product is washed with methanol/water (1:1). The title compound so obtained melts at 254°-255° C. (decomp.), 1H-NMR (DMSO): δ=8.60 (s, 1H); 8.10 (s, 1H); 7.93-7.98 (m, 2H); 7.67-7.83 (m, 6H); 7.32-7.55 (m, 6H); 6.24 (s, 2H).

Workup

filtrationis filtered
filtrationAfter filtration
addition2N sodium hydroxide solution is added until a basic reaction
customis obtained (pH 11)
filtrationFiltration
washthe crystalline product is washed with methanol/water (1:1)

Sources & evidence

ORD record: ord-4423df189bd74b3da494a8c10eec3632
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840911

Reaction notes

Loading…