Chlorine → 3-Nitrobenzonitrile oxide hydrogen chloride

HRID 914984Notes

Reaction equation

HRID 914984 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH:7]=[N:8][OH:9])([O-:3])=[O:2].[Cl:13]Cl>C(Cl)(Cl)Cl>[ClH:13].[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]#[N+:8][O-:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 2191323-Nitrobenzaldoxime

Product 1

HCID 865943233-Nitrobenzonitrile oxide hydrogen chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 79 (1.66 g, 10 mmol) in chloroform (50 mL) was introduced chlorine gas at −5° C. over 15 minutes. The color of the reaction mixture changed from colorless to light blue, green, and finally yellow. After an additional 15 minutes, the reaction mixture was concentrated under reduced pressure to give 80 (2.0 g, 100%) as a yellow oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-75177d0d7499422a9c0fb2de6b66748d
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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