1-Chloro-4-nitrobenzene → HCID 67148374, compound

HRID 747639Notes

Reaction equation

HRID 747639 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.Cl[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.[Cl-].[NH4+]>CS(C)=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([CH:9]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 74741-Chloro-4-nitrobenzeneHCID 23393Picolyl chlorideHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 67148374HCID 67148374, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To 22.44 g of potassium tert-butoxide in 500 ml of dimethyl sulfoxide are slowly added 8.66 g of 4-chloronitrobenzene and 8.2 g of 2-chloromethylpyridine dissolved in 100 ml of dimethyl sulfoxide. After 18 hours at room temperature, the mixture is hydrolysed with saturated ammonium chloride solution and extracted three times with dichloromethane. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is filtered through silica H, eluting with dichloromethane, to give 10.695 g of the expected product.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. filtrationThe residue is filtered through silica H
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-431602d6a320486c997f238286734c0b
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

Loading…