Pyridine → 2-Chloro-5-nitrobenzonitrile

HRID 1744488Notes

Reaction equation

HRID 1744488 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:6])=O.CN(C)C=O.N1C=CC=CC=1.C1(S(Cl)(=O)=O)C=CC=CC=1>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]#[N:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 7369Benzenesulfonyl chlorideHCID 2865622-Chloro-5-nitrobenzamide

Product 1

HCID 855042-Chloro-5-nitrobenzonitrileYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Further, 2-chloro-5-nitrobenzamide (100 g) was added to dimethylformamide (240 ml) and pyridine (100 ml). To the mixture was dropwise added benzenesulfonyl chloride at room temperature with stirring, and the mixture was stirred at 145° C. for 3 h. The reaction mixture was ice-cooled, and water (240 ml) was added thereto. The precipitated crystals were recrystallized from hydrous ethanol to give 2-chloro-5-nitrobenzonitrile (81.3 g), melting point: 108–110° C.

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred at 145° C. for 3 h
  3. temperaturecooled
  4. customThe precipitated crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-525682c8e2124e498cc9a468559b546b
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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