Triethylamine → Pyrazol-1-yl-methyl alpha-(5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitrophenoxy)-propionate
Reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:17]([O-:19])=[O:18])=[C:9]([CH:16]=1)[O:10][CH:11]([CH3:15])[C:12](Cl)=[O:13].[OH:28][CH2:29][N:30]1[CH:34]=[CH:33][CH:32]=[N:31]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:17]([O-:19])=[O:18])=[C:9]([CH:16]=1)[O:10][CH:11]([CH3:15])[C:12]([O:28][CH2:29][N:30]1[CH:34]=[CH:33][CH:32]=[N:31]1)=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of 21.2 g (0.05 mol) of α-(5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-phenoxy)-propionic acid-chloride in 30 ml of toluene was added to a mixture, cooled to from 0° to 5° C., of 5.4 g (0.055 mol) of 1-hydroxymethylpyrazole, 6 g (0.06 mol) of triethylamine and 70 ml of toluene. The reaction mixture was stirred overnight (approx. 15 hours) at room temperature (approx. 20° C.). To work up the mixture, it was diluted with toluene and then washed with water, dilute sodium hydroxide solution and again with water, and the organic phase was dried, filtered and concentrated. 17.0 g (70% of theory) of pyrazol-1-yl-methyl α-(5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitrophenoxy)-propionate were obtained in the form of beige-colored crystals of melting point 75° C.
Workup
- washwashed with water, dilute sodium hydroxide solution and again with water
- customthe organic phase was dried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-799b15f3628a4339a5e26588da276551
- Source dataset
- uspto-grants-1983_09
- Patent number
- US04402727
Reaction notes
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