[CH3:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[OH-].[Na+].[Cl:9][CH2:10][C:11]([N:13]([CH2:22]Cl)[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])=[O:12].[Br-].C([P+](CCCC)(CCCC)C)CCC>ClC1C=CC=CC=1Cl.O>[Cl:9][CH2:10][C:11]([N:13]([CH2:22][N:4]1[CH:3]=[C:2]([CH3:1])[CH:6]=[N:5]1)[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])=[O:12]
A solution of 9.0 parts by weight of 4-methylpyrazole and 4.0 parts by weight of sodium hydroxide in 20 parts by volume of water was added dropwise at 0° C., with vigorous stirring, to a solution of 24.6 parts by weight of 2-chloro-N-chloromethyl-2',6'-dimethylacetanilide and 0.15 part by weight of tri-n-butylmethylphosphonium bromide in 80 parts by volume of o-dichlorobenzene, and the stirring was continued for 5 hours at 10° C. The organic phase was washed with three times 50 parts by volume of water, dried over sodium sulfate and evaporated under reduced pressure at 70° C. to give 25.6 parts by weight of 2-chloro-2',6'-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-acetanilide of melting point 100° C.; the product was pure according to the 1H-NMR spectrum and according to thin layer chromatography carried out using a 3:7 ethyl acetate:toluene mixture.
Loading…
