Dimethylformamide → 2-Chloro-5-nitrobenzamide

HRID 1744487Notes

Reaction equation

HRID 1744487 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](O)=[O:5].C[N:15](C)C=O.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 172872-Chloro-5-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 2865622-Chloro-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloro-5-nitrobenzoic acid (500 g) was added to a mixed solvent of dimethylformamide (500 ml) and toluene (1.5 Liters). Thionyl chloride (217 ml) was added thereto at room temperature with stirring and the mixture was stirred at a refluxing temperature for 3 h. The reaction mixture was then ice-cooled and added dropwise to 28% aqueous amonia (750 ml). The mixture was stirred further for 1 h. The precipitated crystals were collected by filtration, and the crystals were recrystallized from hydrous ethanol to give 2-chloro-5-nitrobenzamide (346 g), melting point: 177–179° C.

Workup

  1. stirringthe mixture was stirred at a refluxing temperature for 3 h
  2. temperatureice-cooled
  3. additionadded dropwise to 28% aqueous amonia (750 ml)
  4. stirringThe mixture was stirred further for 1 h
  5. filtrationThe precipitated crystals were collected by filtration
  6. customthe crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-65857b216ad64087a30579154cd6b030
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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