Water → 1-(8-Cyanooctyl)-2,4,5-triphenyl-imidazole

HRID 265362Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]=[C:11]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C-:33]#[N:34].[Na+].O>CS(C)=O>[C:33]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]=[C:11]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)#[N:34]

Participants

Conditions

Temperature: 50 °C

Procedure

1-(8-Bromooctyl)-2,4,5-triphenylimidazole (4 g) in dimethylsulphoxide (30 ml) was added dropwise to a mixture of sodium cyanide (0.5 g) in dry dimethylsulphoxide (30 ml). The reaction mixture was stirred at 50° C. for 2 h, cooled and poured into water (400 ml). The aqueous was extracted with diethyl ether (4×100 ml), the extracts were combined, washed with water (100 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Chromatography on silica gel eluted with a dichloromethane:methanol gradient and recrystallisation from ether gave 1-(8-cyanoctyl)-2,4,5-triphenylimidazole (1.1 g, 31%) as a white solid, m.p. 72°-73°. Found: C, 83.10; H, 7.21; N, 9.69%; C30H31N3 requires: C, 82.90; H, 7.19; N, 9.57%.

Workup

temperaturecooled
extractionThe aqueous was extracted with diethyl ether (4×100 ml)
washwashed with water (100 ml)
dry with materialdried over anhydrous magnesium sulphate
customevaporated to dryness in vacuo
washChromatography on silica gel eluted with a dichloromethane
custommethanol gradient and recrystallisation from ether

Sources & evidence

ORD record: ord-cc00a0a117f8471d975f962406b6d5b7
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648373

Reaction notes

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