Sodium Cyanide → 3-(5-Bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile

HRID 361914

Reaction equation

[C-:1]#[N:2].[Na+].CS(OC[CH:10]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([Br:21])=[CH:20][C:14]=2[CH:13]=1)(=O)=O.[C:30](OCC)(=O)C.C1(C)C=CC=CC=1>CS(C)=O>[Br:21][C:19]1[CH:18]=[CH:17][C:15]2[S:16][C:12]([CH:11]([CH3:30])[CH:10]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[C:1]#[N:2])=[CH:13][C:14]=2[CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1H-NMR (CDCl3) δ: 3.78 (3H, s), 3.9-4.5 (3H, m), 3.70 (3H, s), 4.3 (2H, m), 6.70-7.80 (8H, m) e) 1.2 g of sodium cyanide was dissolved in 30 ml of dimethyl sulfoxide at a temperature of 90° C. To this was gradually added 18.5 g of 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propyl methanesulfonate, followed by stirring at 80° C. for 1 hour. The resulting reaction solution was mixed with an ethyl acetate/toluene mixture, washed with water, and then dried to distill off the solvent. Crystals thus precipitated were washed with ethanol and dried to obtain 5 g of 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile. The same compound was also obtained with a yield of 2 g, by concentrating the ethanol solution resulting from the washing of crystals and subjecting the concentrate to silica gel column chromatography using chloroform as an elution solvent.

Workup

customThe resulting reaction solution
washwashed with water
customdried
distillationto distill off the solvent
customCrystals thus precipitated
washwere washed with ethanol
customdried

Sources & evidence

ORD record: ord-bd1a795f7ef64356a9bd7fe7a039aee8
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866577

Linked notes

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