Iodoethane → HCID 66986289, compound

HRID 555992Notes

Reaction equation

HRID 555992 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][C:9]1[N:10]=[N:11][NH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:17](I)[CH3:18]>CN(C=O)C>[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][C:9]1[N:10]=[N:11][N:12]([CH2:17][CH3:18])[N:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 20043629Carbamic acid, (1H-tetrazol-5-ylmethyl)-, 1,1-dimethylethyl ester (9CI)

Product 1

HCID 66986289HCID 66986289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2H-Tetrazol-5-ylmethyl)-carbamic acid tert-butyl ester (0.9 g, 4.5 mmol) is dissolved in dry DMF, NaH (60% dispersed in mineral oil) (0.18 g, 4.5 mmol) is added and the reaction mixture is stirred at room temperature for 5 minutes before ethyl iodide (0.35 ml, 4.5 mmol) is added. The reaction mixture is stirred overnight at room temperature and partitioned between EtOAc and water. The organic phase is dried over MgSO4, filtered and concentrated in vacuo to afford an oil. Purification by flash chromatography on silica eluting with 2:1 iso-hexanes/EtOAc affords the title compound.

Workup

  1. additionis added
  2. custompartitioned between EtOAc and water
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford an oil
  7. customPurification by flash chromatography on silica eluting with 2:1 iso-hexanes/EtOAc

Sources & evidence

ORD record
ord-1ed168d17cc84b029f311da8a95a9ac6
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

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