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

HRID 567879Notes

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-005140692c7c426fa7acaf2cac386e02
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180659B2

Reaction notes

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