Hydrochloric Acid → HCID 21520616, compound

HRID 1282939Notes

Reaction equation

HRID 1282939 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.[CH3:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[C:14]([O:21]C(=O)C)[CH:13]=1.Cl>CN(C)C1C=CC=CC=1.CC(C)=O.[OH-].[Na+]>[Cl:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([Cl:10])[C:5]=1[OH:9])[NH:1][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:12]([CH3:11])=[CH:13][C:14]=1[OH:21]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 800374-Amino-2,6-dichlorophenolHCID 12366428HCID 12366428, compound

Product 1

HCID 21520616HCID 21520616, compoundYield 72.5%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 949N,N-DimethylanilineSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Amino-2,6-dichlorophenol (16 g.) was put into solution in N,N-dimethylaniline (15 ml.) and acetone (200 ml.), to which the acetone solution of 4-methyl-2-acetoxybenzoyl chloride was added dropwise. After reaction for several hours, by condensing and then acidifying the solution with 4 N hydrochloric acid a precipitate was obtained, which was redissolved in 2 N sodium hydroxide solution. The solution was made acidic with dilute hydrochloric acid, thereby precipitating the product which was recrystallized from aqueous acetone to give white crystals (20.3 g.) of 3',5'-dichloro-2,4'-dihydroxy-4-methylbenzanilide. Yield: 72.5%. The melting point was 246°-247° C.

Workup

  1. customAfter reaction for several hours
  2. customby condensing
  3. customwas obtained
  4. customprecipitating the product which
  5. customwas recrystallized from aqueous acetone

Sources & evidence

ORD record
ord-79d30ece161c45e1b6a243eef462dc02
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

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