Dimethylformamide → 5-Chloro-2,4-dinitrobenzamide

HRID 2288019Notes

Reaction equation

HRID 2288019 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Cl:16])=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].C[N:18](C=O)C.[OH-].[NH4+]>S(Cl)(Cl)=O.CC(C)=O>[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Cl:16])=[CH:9][C:5]=1[C:6]([NH2:18])=[O:7])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 37278605-chloro-2,4-dinitrobenzoic acid

Product 1

HCID 148972315-Chloro-2,4-dinitrobenzamideYield 84%

Reagents, catalysts & solvents 2

HCID 24386Thionyl ChlorideCatalystHCID 180AcetoneSolvent

Procedure

2,4-Dinitro-5-chlorobenzoic acid (7.00 g, 28.4 mmol) was suspended in 40 mL thionyl chloride containing 3 drops of DMF. The suspension was warmed to reflux for four hours. After cooling to room temperature, solvent was removed by rotary evaporation leaving a golden yellow liquid. This was diluted with 30 mL acetone and added dropwise over 20 minutes to a 0° C. solution of 20 mL concentrated ammonium hydroxide. The reaction was stirred at 0° C. for 30 minutes, then poured into 250 g of ice. The yellow orange precipitate was collected by filtration and washed well with water. The solid was dried first by water aspirator then under high vacuum to furnish 5.9 g (24 mmol, 84% yield) of product. NMR (400 MHz; acetone-d6): δ 8.75, s 1H, 8.25, s 1H; mp 201-203° C.

Workup

  1. temperatureThe suspension was warmed
  2. temperatureto reflux for four hours
  3. customsolvent was removed by rotary evaporation
  4. customleaving a golden yellow liquid
  5. filtrationThe yellow orange precipitate was collected by filtration
  6. washwashed well with water
  7. dry with materialThe solid was dried first by water aspirator then under high vacuum

Sources & evidence

ORD record
ord-cb1a0236540d47a7867bff0c669ea6a6
Source dataset
uspto-grants-2000_07
Patent number
US06087368

Reaction notes

Loading…