Sodium Cyanide → 2-(3,5-Dimethoxyphenylthio)-benzyl cyanide

HRID 2299185Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14]Br)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C-:20]#[N:21].[Na+]>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][C:20]#[N:21])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(3,5-Dimethoxyphenylthio)benzyl bromide (9.53 g) was dissolved in dimethyl sulfoxide (90 ml), sodium cyanide (2.77 g) was added thereto and the mixture was stirred at 80° C. for 1.5 hours. The reaction solution was diluted with ethyl acetate, washed with water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1) to give 2-(3,5-dimethoxyphenylthio)-benzyl cyanide (4.91 g, yield of 61%).

Workup

washwashed with water and saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated in vacuo
customThe residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-c641c37130d549e6b3a81005e6ca2f61
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495592B1

Reaction notes

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