Acetamide, 2-chloro-N-(chloromethyl)-N-(2-ethyl-6-methylphenyl)- → 2-chloro-2'-methyl-6'-ethyl-N-(4-chloro-3,5-dimethylpyrazol-1-yl-methyl)-acetanilide
Reaction equation
[Cl:1][CH2:2][C:3]([N:5]([CH2:15]Cl)[C:6]1[C:11]([CH2:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:14])=[O:4].[Cl:17][C:18]1[C:19]([CH3:24])=[N:20][NH:21][C:22]=1[CH3:23]>COCCOC>[Cl:1][CH2:2][C:3]([N:5]([CH2:15][N:20]1[C:19]([CH3:24])=[C:18]([Cl:17])[C:22]([CH3:23])=[N:21]1)[C:6]1[C:11]([CH2:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:14])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
21.4 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-chloromethyl acetanilide and 20.2 parts by weight of 4-chloro-3,5-dimethylpyrazole are refluxed for 10 hours in 100 parts by volume of glycol dimethyl ether. After cooling the mixture to 0° C., it is filtered, and the filtrate, concentrated to 23.8 parts by weight, is filtered with 600 parts by volume of chloroform through 50 parts by weight of silica gel. From the concentrated chloroform filtrate there is isolated 20.4 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-(4-chloro-3,5-dimethylpyrazol-1-yl-methyl)-acetanilide as an oil which completely crystallizes upon milling with 50 ml of petroleum ether (m.p. 66° C. from petroleum ether).
Workup
- filtrationit is filtered
- concentrationthe filtrate, concentrated to 23.8 parts by weight
- filtrationis filtered with 600 parts by volume of chloroform through 50 parts by weight of silica gel
Sources & evidence
- ORD record
- ord-c1f449e4e8f649f4b4bf9c686a4df531
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04593104
Reaction notes
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