Iodoethane → HCID 67160209, compound

HRID 601632Notes

Reaction equation

HRID 601632 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[NH:14][N:13]=[N:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18](I)[CH3:19]>C1COCC1.C(OC(=O)C)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[N:12][N:13]([CH2:18][CH3:19])[N:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178453348HCID 178453348, compound

Product 1

HCID 67160209HCID 67160209, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [2-(1H-Tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester (EP 449523) (1.0 g, 4.69 mmol) in dry THF (20 ml) is treated with a 60% dispersion of sodium hydride in mineral. oil (0.19 g, 4.69 mmol) and stirred at ambient temperature for 10 minutes. Ethyliodide (0.375 ml, 4.69 mmol) is added and the reaction mixture is heated at reflux for 7 hours, then diluted with ethylacetate and filtered. The filtrate is evaporated and the residue purified by flash silica chromatography (elution 3:2 hexanelethylacetate) to afford [2-(2-Ethyl-2H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester, which elutes first, and the titled compound, [2-(1-Ethyl-1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester, which elutes next.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 7 hours
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue purified by flash silica chromatography (elution 3:2 hexanelethylacetate)

Sources & evidence

ORD record
ord-c9bf2c3934c041ddb443f136780d0504
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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