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

HRID 1901344Notes

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

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-5813034b79124ce0bfa89e18b52c2a2c
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576343

Reaction notes

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