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Triethylamine → 5-{2,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethyloxy]-benzoyloxy}-1,3-dimethylpyrazole

HRID 659931
Notes
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Reaction equation

HRID 659931 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 574372552,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoyl chlorideHCID 178429390HCID 178429390, compound

Product 1

HCID 592816475-{2,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethyloxy]-benzoyloxy}-1,3-dimethylpyrazoleYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

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

  1. customAfter the reaction
  2. extractionthe mixture was extracted with ethyl acetate (100 ml)
  3. washwashed with diluted hydrochloric acid
  4. dry with materialan aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate
  5. distillationEthyl acetate was distilled off

Sources & evidence

ORD record
ord-1fd6f5b04d554a348e268f894dbb74ba
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084398B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes