Hydrochloric Acid → HCID 45117928, compound

HRID 358725Notes

Reaction equation

HRID 358725 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([NH:7][CH3:8])=[CH:5][C:4]=1[CH3:11].B(Cl)(Cl)Cl.[Cl:16][CH2:17][C:18]#N.Cl.[OH-:21].[Na+]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:16][CH2:17][C:18]([C:9]1[CH:10]=[C:3]([O:2][CH3:1])[C:4]([CH3:11])=[CH:5][C:6]=1[NH:7][CH3:8])=[O:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 23128101HCID 23128101, compound

Product 1

HCID 45117928HCID 45117928, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

4-Methoxy-3-methyl-N-methylaniline (30.2 g) is added dropwise to a stirred solution of boron trichloride (26 g) in toluene (100 ml) cooled to 0 to 5°. Chloroacetonitrile (19.9 g) and then titanium tetrachloride (26.8 ml) are added and the mixture is heated under reflux for 6 hours. After cooling to ambient temperature, hydrochloric acid (2M, 500 ml) is added and the mixture then heated to 80° for 30 minutes. The mixture is cooled to ambient temperature, sodium hydroxide (2M) is added to pH 3 and the mixture then extracted with dichloromethane (3×300 ml). The combined extracts are washed with water (100 ml) and dried over magnesium sulphate. The solvent is removed by distillation and the residue purified to give the novel compound 2-chloro-5'-methoxy-4'-methyl-2'-(methylamino)acetophenone.

Workup

  1. temperaturecooled to 0 to 5°
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 6 hours
  4. temperaturethe mixture then heated to 80° for 30 minutes
  5. temperatureThe mixture is cooled to ambient temperature
  6. extractionthe mixture then extracted with dichloromethane (3×300 ml)
  7. washThe combined extracts are washed with water (100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customThe solvent is removed by distillation
  10. customthe residue purified

Sources & evidence

ORD record
ord-b2539dca173d44f9a4e41f567371a474
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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