Hydrochloric Acid → HCID 21520612, compound

HRID 1282936Notes

Reaction equation

HRID 1282936 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.CN(C)C1C=CC=CC=1.[C:20]([C:23]1[CH:31]=[C:27](C(Cl)=O)[C:26]([OH:32])=[C:25](C(=O)C)[C:24]=1[OH:36])(=[O:22])C.Cl.[OH-].[Na+]>CC(C)=O>[Cl:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([Cl:10])[C:5]=1[OH:9])[NH:1][C:20](=[O:22])[C:23]1[CH:31]=[CH:27][C:26]([OH:32])=[CH:25][C:24]=1[OH:36]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 949N,N-DimethylanilineHCID 14798Sodium HydroxideHCID 800374-Amino-2,6-dichlorophenolHCID 131710415HCID 131710415, compound

Product 1

HCID 21520612HCID 21520612, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent4×

Procedure

4-Amino-2,6-dichlorophenol (10 g.) and N,N-dimethylaniline (10 ml.) were dissolved in acetone (100 ml.) to which, with stirring and under cooling at 0°-4° C., the acetone solution of diacetyl-β-resorcyloyl chloride was added dropwise. After several hours, the reaction mixture was made acidic with hydrochloric acid, and was subjected to evaporation under reduced pressure until the volume was halved. The resultant solution was added to 1 liter of 4 N hydrochloric acid and allowed to stand in the cold. Precipitates were obtained and dissolved in acetone. The acetone solution was made alkaline with 2 N sodium hydroxide and stirred for several hours at room temperature. Acidifying the solution to pH 1-2 with dilute hydrochloric acid gave precipitate which was recrystallized in aqueous acetone to give light yellow prism-like crystals of 3',5'-dichloro-2,4,4'- trihydroxybenzanilide (13.2 g.). Yield: 84.8%. The melting point is 235°- 237° C.

Workup

  1. temperatureunder cooling at 0°-4° C.
  2. waitAfter several hours
  3. customwas subjected to evaporation under reduced pressure until the volume
  4. additionThe resultant solution was added to 1 liter of 4 N hydrochloric acid
  5. customPrecipitates
  6. customwere obtained
  7. stirringstirred for several hours at room temperature
  8. customgave precipitate which
  9. customwas recrystallized in aqueous acetone

Sources & evidence

ORD record
ord-6b9d1dc461b041309ceb78e383f86856
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

Loading…