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

HRID 1256102Notes

Reaction equation

HRID 1256102 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 133.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-5-nitrobenzonitrile (50 g, 0.15 mol) in MeCN (1000 mL) was added K2CO3 (45.5 g, 0.33 mol) and phenylmethanethiol (34 g, 0.27 mol). The mixture was stirred at room temperature overnight. The mixture was filtered through the celite pad and the filtrate was concentrated in vacuo to give 2-(benzylthio)-5-nitrobenzonitrile (54 g, 73%) as a yellow solid. 1H NMR CDCl3 400 MHz δ 8.43 (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-3ee30fd60010400eb802dfdfcbcb67c7
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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