Benzene → 3-[N-(alpha-chloroacetyl)-2-methyl-4-chloroanilino]propionaldehyde
Reaction equation
[CH3:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[NH:4][CH2:5][CH2:6][CH:7]=[O:8].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:26][CH2:27][C:28](Cl)=[O:29]>O>[Cl:26][CH2:27][C:28]([N:4]([CH2:5][CH2:6][CH:7]=[O:8])[C:3]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=1[CH3:1])=[O:29]Participants
Procedure
The diethyl acetal of 3-(2-methyl-4-chloroanilino)propionaldehyde (0.2 mole), benzene (150 ml) and sodium carbonate (0.2 mole) dissolved in water (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The mixture is cooled in an ice bath and chloroacetyl chloride (0.2 mole) is added dropwise with stirring. After addition is completed stirring is continued and the reaction mixture is allowed to warm up to room temperature. After this time the mixture is filtered and the filtrate washed with dilute aqueous hydrochloric acid. The washed filtrate is dried over anhydrous magnesium sulphate and is stripped of solvent under reduced pressure to yield the desired product the diethyl acetal of 3-[N-(α-chloroacetyl)-2-methyl-4-chloroanilino]propionaldehyde.
Workup
- additionare charged into a glass reaction vessel
- customequipped with a mechanical stirrer
- additionthermometer and addition funnel
- temperatureThe mixture is cooled in an ice bath
- additionAfter addition
- stirringis completed stirring
- filtrationAfter this time the mixture is filtered
- washthe filtrate washed with dilute aqueous hydrochloric acid
- dry with materialThe washed filtrate is dried over anhydrous magnesium sulphate
Sources & evidence
- ORD record
- ord-cce2c93df68940aaa0229d13e320629c
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03983174
Reaction notes
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