Chloroacetyl chloride → N-alpha-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH3:15].C(=O)(O)[O-].[Na+].O1CCOCC1.[Cl:27][CH2:28][C:29](Cl)=[O:30]>CCOCC.O>[Cl:27][CH2:28][C:29]([N:7]([CH2:6][CH:2]1[O:3][CH2:4][CH2:5][O:1]1)[C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH3:15])=[O:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
N-(1,3-Dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline (8 grams), sodium bicarbonate (7 grams), dioxane (50 ml) and water (4 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. This mixture was cooled to a temperature of about 0°C and chloroacetyl chloride (4.3 grams) was added, with stirring, over a period of about 15 minutes. After the addition was completed stirring was continued for a period of about 1 hour. After this time ether (100 ml) was added to the mixture and the resulting solution was washed with water. The washed solution was then dried over anhydrous magnesium sulfate and stripped of solvents leaving a solid residue. The residue was recrystallized from hexane to yield the desired product N-α-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline having a melting point of 88° to 89°C.
Workup
- customequipped with a mechanical stirrer
- additionwas added
- additionAfter the addition
- stirringwas completed stirring
- waitwas continued for a period of about 1 hour
- washthe resulting solution was washed with water
- dry with materialThe washed solution was then dried over anhydrous magnesium sulfate
- customleaving a solid residue
- customThe residue was recrystallized from hexane
Sources & evidence
- ORD record
- ord-077f4db60bb546b2bfbcc593fffbc83f
- Source dataset
- uspto-grants-1976_03
- Patent number
- US03942972
Reaction notes
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