Triethylamine → 5-{2,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethyloxy]-benzoyloxy}-1,3-dimethylpyrazole
Reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[C:9]([Cl:19])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:20][N:21]1[C:25]([OH:26])=[CH:24][C:23]([CH3:27])=[N:22]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[C:9]([Cl:19])[CH:8]=[CH:7][C:3]=1[C:4]([O:26][C:25]1[N:21]([CH3:20])[N:22]=[C:23]([CH3:27])[CH:24]=1)=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoyl chloride (0.60 g) was dissolved in tetrahydrofuran (5 ml), this solution was added dropwise to a tetrahydrofuran (5 ml) solution of 1,3-dimethyl-5-hydroxypyrazole (0.22 g) and triethylamine (0.23 g) at 5° C. and the mixture was stirred at room temperature for 6 hours. After the reaction, the mixture was extracted with ethyl acetate (100 ml) and then washed with diluted hydrochloric acid and an aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off to obtain the desired 5-{2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethyloxy]-benzoyloxy}-1,3-dimethylpyrazole (0.65 g).
Workup
- customAfter the reaction
- extractionthe mixture was extracted with ethyl acetate (100 ml)
- washwashed with diluted hydrochloric acid
- dry with materialan aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate
- distillationEthyl acetate was distilled off
Sources & evidence
- ORD record
- ord-1fd6f5b04d554a348e268f894dbb74ba
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084398B2
Reaction notes
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