Benzyl mercaptan → 2-(benzylthio)-5-nitrobenzonitrile

HRID 1256070Notes

Reaction equation

HRID 1256070 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[C:19]1([CH2:25][SH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC#N>[CH2:25]([S:26][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 7067652-(benzylthio)-5-nitrobenzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-5-nitrobenzonitrile (27.375 g, 0.15 mol) in MeCN (500 ml) was added K2CO3 (24.84 g, 0.18 mol) and phenylmethanethiol (17.71 ml, 0.15 mol). The solution was stirred at room temperature for overnight. The mixture was filtered through the celite pad and the filtrate was concentrated in vacuo to give 2-(benzylthio)-5-nitrobenzonitrile (40.5 g, 100%) as a yellow solid. 1H NMR: CDCl3 400 MHz δ8.43 (s, 1H), 8.27-8.25 (m, 1H), 7.44-7.31 (m, 6H), 4.35 (s, 2H).

Workup

  1. filtrationThe mixture was filtered through the celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c72a1f152e1a413e80563dc7186df572
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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