Pyridine → 3-(N-chloroacetyl-2,6-dimethylphenylamino)-2-butanone O-methyloxime
Reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].N1C=CC=CC=1.[CH3:12][O:13][N:14]=[C:15]([CH:17]([NH:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27])[CH3:18])[CH3:16]>C1C=CC=CC=1>[CH3:12][O:13][N:14]=[C:15]([CH:17]([N:19]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27])[C:3](=[O:4])[CH2:2][Cl:1])[CH3:18])[CH3:16]Participants
Procedure
A sample of 54.2 g (0.048 mol) chloroacetyl chloride and a sample of 34.8 g (0.44 mol) pyridine was added over a 25-minute period to a solution of 97.0 g (0.44 mol) 3-(2,6-dimethylphenylamino)-2-butanone O-methyloxime maintained at 45° C. in 500 ml benzene. The pyridine was added slightly faster than the chloroacetyl chloride. The reaction temperature rose to about 50°-58° C. during the addition. The reaction mixture was then cooled, washed with water, washed with 5% aqueous sodium bicarbonate solution, stirred with silica gel, filtered and evaporated under reduced pressure to give 111.5 g of 3-(N-chloroacetyl-2,6-dimethylphenylamino)-2-butanone O-methyloxime, as an oil. The infrared spectrum of the product showed carbonyl absorption at 5.9 micron and O--CH3 absorption at 9.5 micron. The product is tabulated in Table I as Compound No. 5-B.
Workup
- additionThe reaction temperature rose to about 50°-58° C. during the addition
- temperatureThe reaction mixture was then cooled
- washwashed with water
- washwashed with 5% aqueous sodium bicarbonate solution
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-5ae24b5bffc64bd0b6d4057145ef91b3
- Source dataset
- uspto-grants-1979_11
- Patent number
- US04174210
Reaction notes
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