3,4-Dimethylaniline → 3-chloro-n-(3,4-dimethylphenyl)propanamide

HRID 1076923Notes

Reaction equation

HRID 1076923 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[Cl:10][CH2:11][CH2:12][C:13](Cl)=[O:14]>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][C:13](=[O:14])[CH2:12][CH2:11][Cl:10])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 72483,4-DimethylanilineHCID 693643-Chloropropionyl chloride

Product 1

HCID 2265843-chloro-n-(3,4-dimethylphenyl)propanamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3,4-Dimethylaniline (25.5 grams), β-chloropropionyl chloride (20 grams) and benzene (100 ml) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is stirred at reflux for a period of about 3 hours. After this time the reaction mixture is cooled to room temperature and is washed with aqueous sodium bicarbonate, dilute hydrochloric acid and water. The washed mixture is then dried over anhydrous magnesium sulfate, is filtered and stripped of benzene under reduced pressure to yield the desired product N-(3,4-dimethylphenyl)-β-chloropropionamide as the residue.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureat reflux for a period of about 3 hours
  4. washis washed with aqueous sodium bicarbonate, dilute hydrochloric acid and water
  5. dry with materialThe washed mixture is then dried over anhydrous magnesium sulfate
  6. filtrationis filtered

Sources & evidence

ORD record
ord-00e7f2f6a055434a88d4145ac5b2530b
Source dataset
uspto-grants-1976_05
Patent number
US03958974

Reaction notes

Loading…