2,3-Dichlorobenzoic acid → HCID 86589047, compound

HRID 916237Notes

Reaction equation

HRID 916237 reaction equation
[N+]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.Cl[C:12]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[C:5]1([NH:6][C:20]2([Cl:21])[CH:19]=[CH:18][CH:17]=[C:13]([C:14]([OH:16])=[O:15])[CH2:12]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:4]=1

Participants

5

Reactant 3

HCID 57652,3-Dichlorobenzoic acidHCID 69462-NitroanilineHCID 10340Sodium Carbonate

Product 1

HCID 86589047HCID 86589047, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 20.0 g (0.145 mole) of 2-nitroaniline 1, 28.0 g (0.146 mole) of 2,3-dichlorobenzoic acid in 200 mL dry dimethyl sulfoxide, 20.0 g (0.19 mole) of anhydrous sodium carbonate is added. The reaction mixture is heated at 110° C. for 5 hours under nitrogen atmosphere. The dimethyl sulfoxide solvent from the reaction mixture is removed under high vacuum and dried. The crude product is extracted three times each time with 100 mL methylene chloride by partitioning into water. The combined methylene chloride layer is dried over anhydrous sodium sulfate and filtered. Solvent from the filtrate is removed under reduced pressure and dried. The crude residue is chromatographed on a silica gel 60 column (230-400 mesh) using 25% ethyl acetate in hexane as an elution solvent. The fractions containing the desired product are combined and the solvent removed under reduced pressure to yield 20.0 g (47%) of N-phenyl N-(1-chloro 3-carboxyphenyl) amine 9.

Workup

  1. customThe dimethyl sulfoxide solvent from the reaction mixture is removed under high vacuum
  2. customdried
  3. extractionThe crude product is extracted three times each time with 100 mL methylene chloride
  4. customby partitioning into water
  5. dry with materialThe combined methylene chloride layer is dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customSolvent from the filtrate is removed under reduced pressure
  8. customdried
  9. customThe crude residue is chromatographed on a silica gel 60 column (230-400 mesh)
  10. additionThe fractions containing the desired product
  11. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0b49880a4abe45e98ceec2d09c4d23f0
Source dataset
uspto-grants-2007_09
Patent number
US07268220B2

Reaction notes

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