Hydrochloric Acid → HCID 20327564, compound

HRID 372492Notes

Reaction equation

N[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.C[N:12]([CH3:19])C1C=CC=CC=1.C([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)C.Cl.[OH-:38].[Na+]>CC(C)=O>[Cl:10][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([Cl:8])[C:5]=1[OH:9])[C:19]([NH:12][C:27]1[CH:31]=[CH:23][C:24]([OH:36])=[CH:25][C:26]=1[OH:32])=[O:38]

Participants

Conditions

Temperature: 2 °C

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

waitAfter several hours
customwas subjected to evaporation under reduced pressure until the volume
additionThe resultant solution was added to 1 liter of 4 N hydrochloric acid
customPrecipitates
customwere obtained
stirringstirred for several hours at room temperature
customgave precipitate which
customwas recrystallized in aqueous acetone

Sources & evidence

ORD record: ord-2fc9d110dfbc4744aa6c6aee7e413364
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04091097

Reaction notes

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