Sodium Iodide → ethyl 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoate

HRID 659934Notes

Reaction equation

[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.Br[CH2:7][CH2:8][O:9][C:10]1[C:11]([Cl:22])=[C:12]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[Cl:22][C:11]1[C:10]([O:9][CH2:8][CH2:7][N:1]2[CH:5]=[N:4][N:3]=[N:2]2)=[C:20]([Cl:21])[CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl:22][C:11]1[C:10]([O:9][CH2:8][CH2:7][N:2]2[NH:3][N:4]=[CH:5][NH:1]2)=[C:20]([Cl:21])[CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 80 °C

Procedure

1H-tetrazol (0.45 g) and ethyl 3-(2-bromoethoxy)-2,4-dichlorobenzoate (2.00 g) were suspended in DMF (15 ml), potassium carbonate (1.21 g) and sodium iodide (0.04 g) were added thereto and the mixture was stirred at 80° C. for 3 hours. After the reaction, cool water was added, extracted with ethyl acetate (100 ml) and dried over anhydrous magnesium sulfate. The residue obtained by distilling off ethyl acetate was purified with silica gel column chromatography (elution solvent; ethyl acetate: hexane=1:1) to obtain the desired ethyl 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoate (0.88 g) and ethyl 2,4-dichloro-3-[2-(1H-tetrazol-2-yl)ethoxy]benzoate (0.99 g).

Workup

customAfter the reaction
additionwas added
extractionextracted with ethyl acetate (100 ml)
dry with materialdried over anhydrous magnesium sulfate
customThe residue obtained
distillationby distilling off ethyl acetate
customwas purified with silica gel column chromatography (elution solvent; ethyl acetate: hexane=1:1)

Sources & evidence

ORD record: ord-21b447b0c93749c0a26ac60350a7749f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084398B2

Reaction notes

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