2-Nitrobenzenesulfenyl chloride → 3-(2-Nitro-phenylsulfanyl)-1H-indole-6-carbonitrile

HRID 1645187Notes

Reaction equation

HRID 1645187 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[CH:2]1.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]Cl)([O-:14])=[O:13]>C(OCC)C>[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 243192-Nitrobenzenesulfenyl chlorideHCID 851461H-indole-6-carbonitrile

Product 1

HCID 667756173-(2-Nitro-phenylsulfanyl)-1H-indole-6-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1H-indole-6-carbonitrile (1.00 g, 7.04 mmol) in diethyl ether (50 mL) was added at rt 2-nitrobenzenesulfenyl chloride (1.34 g, 7.04 mmol) and the reaction mixture was stirred for 18 hrs. The mixture was concentrated and the crude product was purified using column chromatography (ethyl acetate/heptane 1:4→4:1) to give 3-(2-Nitro-phenylsulfanyl)-1H-indole-6-carbonitrile (1.62 g, 5.49 mmol, 78%).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-92efa3ac0435403aa4d8fb6040846ee0
Source dataset
uspto-grants-2012_02
Patent number
US08124647B2

Reaction notes

Loading…