Water → 2-chloro-2',6'-dimethyl-N-(4,5-dichloroimidazol-1-yl-methyl)-acetanilide
Reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[Na+].O.[Cl:11][CH2:12][C:13]([N:15]([CH2:24]Cl)[C:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:23])=[O:14]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl>[Cl:11][CH2:12][C:13]([N:15]([CH2:24][N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]=[CH:4]1)[C:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:23])=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 13.7 parts by weight of 4,5-dichloroimidazole and 4.4 parts by weight of sodium hydroxide in 20 parts of water was added dropwise to a solution of 24.6 parts by weight of 2-chloro-N-chloromethyl-2',6'-dimethylacetanilide and 2.0 parts by weight of triethylbenzylammonium chloride in 50 parts by volume of dichloromethane at 20°-25° C., with vigorous stirring, which was continued for 2 hours. The organic phase was washed with three times 30 parts by volume of water, dried over sodium sulfate and evaporated under reduced pressure at 70° C., to give 29.9 parts by weight of 2-chloro-2',6'-dimethyl-N-(4,5-dichloroimidazol-1-yl-methyl)-acetanilide of melting point 99° C.; the product was pure according to the 1H-NMR spectrum and according to thin layer chromatography carried out with a 3:7 ethyl acetate:toluene mixture.
Workup
- washThe organic phase was washed with three times 30 parts by volume of water
- dry with materialdried over sodium sulfate
- customevaporated under reduced pressure at 70° C.
Sources & evidence
- ORD record
- ord-32fb8418b39a4bccad0705c2b7b58862
- Source dataset
- uspto-grants-1982_03
- Patent number
- US04321395
Reaction notes
Loading…