Water → 1-(7-Cyanoheptyl)-2,4,5-triphenylimidazole

HRID 265367Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

1-(7-Bromoheptyl)-2,4,5-triphenylimidazole (7 g) in dry dimethylsulphoxide (15 ml) was added over 20 minutes to a mixture of sodium cyanide (0.87 g) in dimethyl-sulphoxide (25 ml). The reaction was stirred at 40° C. for 1 hour. The cooled reaction mixture was poured into water (800 ml) and extracted with diethyl ether (4×100 ml). The extracts were combined, washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Recrystallisation from dichloro-methane/hexane gave 1-(7-cyanoheptyl)-2,4,5-triphenylimidazole (3.7 g,60%) as a white solid, m.p. 93°-94°; Found: C, 82.35; H, 6.90; N, 9.96%; C29H29N3 1% CH2Cl2 requires C, 82.43; H, 6.91; N, 9.91%.

Workup

customThe cooled reaction mixture
extractionextracted with diethyl ether (4×100 ml)
washwashed with water
dry with materialdried over anhydrous magnesium sulphate
customevaporated to dryness in vacuo
customRecrystallisation from dichloro-methane/hexane

Sources & evidence

ORD record: ord-c04226f7763a4e989bb34ca71d14e1e3
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648373

Reaction notes

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