Toluene → HCID 68542665, compound

HRID 1931786Notes

Reaction equation

HRID 1931786 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].O=[C:11]([CH2:17][CH3:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14].C1(C)C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:11]([CH2:17][CH3:18])=[CH:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 122813,5-DichloroanilineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 68542665HCID 68542665, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst2×HCID 962WaterSolvent

Procedure

In a 300 mL-flask were placed 3,5-dichloroaniline (25.0 g, 154 mmol), methyl 3-oxopentanoate (22.1 g, 170 mmol) and toluene (160 mL). To this solution was added p-toluenesulphonic acid monohydrate (0.59 g, 3.1 mmol), and the resulting mixture was heated in a bath kept at 100° C. under a reduced pressure of 21 kPa for 3 hours, while the water generated was taken out of the reaction system by using a Dean-Stark trap under reflux. p-Toluenesulphonic acid monohydrate (0.59 g, 3.1 mmol) was then added, and reflux was continued for 1 hour. The heating was then discontinued, nitrogen leaked in, and the reaction mixture cooled. After distillation of the solvent under reduced pressure, the residue was distilled under reduced pressure to give 27.4 g of the title compound. The yield was 64.8%.

Workup

  1. temperaturethe resulting mixture was heated in a bath
  2. temperatureunder reflux
  3. temperaturereflux
  4. temperaturecooled
  5. distillationAfter distillation of the solvent under reduced pressure
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-89a49ec3b9944715968d7c79ef007faa
Source dataset
uspto-grants-2012_05
Patent number
US08188307B2

Reaction notes

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