Water → 2-(8-Cyanooctyl)-4,5-diphenyltriazole

HRID 265407

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

2-(8-Bromooctyl)-4,5-diphenyltriazole (7 g) in dimethylsulphoxide (220 ml) was added to a suspension of sodium cyanide (1 g) in dimethylsulphoxide (60 ml) over 15 minutes. The reaction mixture was stirred at 24° C. for 1 hour and at 50° C. for 2 hours. The cooled reaction mixture was poured into water (600 ml), extracted with diethyl ether (4×200 ml). The extracts were combined, washed with water (100 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Column chromatography on silica gel eluted with a hexane:ethyl acetate gradient gave 2-(8-cyanooctyl)-4,5-diphenyl-triazole (5.6 g, 92%) as an oil.

Workup

customThe cooled reaction mixture
extractionextracted with diethyl ether (4×200 ml)
washwashed with water (100 ml)
dry with materialdried over anhydrous magnesium sulphate
customevaporated to dryness in vacuo
washColumn chromatography on silica gel eluted with a hexane

Sources & evidence

ORD record: ord-a3a00b3c0f3a4e65838f61f096fb530e
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648373

Linked notes

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