N,N-Dimethylaniline → HCID 21520618, compound

HRID 1282942Notes

Reaction equation

HRID 1282942 reaction equation
C([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=O)(=O)C.S(Cl)(Cl)=O.[CH3:18][C:19]1[CH:24]=[C:23]([NH2:25])[CH:22]=[C:21]([Cl:26])[C:20]=1[OH:27].CN(C)C1C=CC=CC=1.C(OC1C(=CC=CC=1)C(Cl)=O)(=O)C>CC(C)=O>[Cl:26][C:21]1[CH:22]=[C:23]([CH:24]=[C:19]([CH3:18])[C:20]=1[OH:27])[NH:25][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=1[OH:4]

Participants

7

Reactant 5

HCID 949N,N-DimethylanilineHCID 2244AspirinHCID 24386Thionyl ChlorideHCID 796682-Acetoxybenzoyl chlorideHCID 27744394-Amino-2-chloro-6-methylphenol

Product 1

HCID 21520618HCID 21520618, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

Acetylsalicyclic acid (1.39g.) was converted to its acid chloride by conventional method using thionyl chloride and put in solution in acetone (25 ml.). 2-Methyl-4-amino-6-chlorophenol (1.35 g.) and N,N-dimethylaniline (about 1 ml.) were dissolved in acetone to which, with stirring in the cold at 1° to 2° C., the above-prepared acetone solution of acetylsalicyloyl chloride was added dropwise over 20-30 minutes, and reaction was continued for 1-2 hours. Then under reduced pressure the acetone was evaporated off, and the residue was put in solution in 2 N sodium hydroxide by stirring several hours at room temperature. Addition of 2 N hydrochloric acid to make the pH of the solution lower than 1 resulted in the formation of a precipitate which was recrystallized from aqueous acetone to give white crystals (1.08 g.) of 3'-chloro-2,4'-dihydroxy-5'-methylbenzanilide. Yield: 45.4%. Melting point: 192°-194° C.

Workup

  1. customreaction
  2. customThen under reduced pressure the acetone was evaporated off
  3. stirringby stirring several hours at room temperature
  4. additionAddition of 2 N hydrochloric acid
  5. customresulted in the formation of a precipitate which
  6. customwas recrystallized from aqueous acetone

Sources & evidence

ORD record
ord-a14cb5f26acd4412a400f05809986286
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

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