Iodoethane → tert-Butyl ethyl(prop-2-en-1-yl)carbamate

HRID 1432119Notes

Reaction equation

HRID 1432119 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH:9]=[CH2:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].[CH2:16](I)[CH3:17]>CN(C=O)C.C1COCC1.O>[C:1]([O:5][C:6](=[O:11])[N:7]([CH2:8][CH:9]=[CH2:10])[CH2:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 71365398tert-Butyl ethyl(prop-2-en-1-yl)carbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 31.44 g allyl-carbamic acid tert-butyl ester (200 mmol) in 300 ml DMF and 30 ml dry THF is treated with 12 g (300 mmol) NaH (60% suspension in mineral oil). The temperature is kept below 40° C. with an cold water bath. When the development of hydrogen gas ceased the reaction mixture is treated, under ice cooling, with 24 ml (300 mmol) ethyl iodide. After 16 h the mixture is diluted with 1 L water and extracted with TBME. The organic layer is washed extensively with water, concentrated under reduced pressure and distilled at 0.3 mmHg, bp. 38-39°, to yield the allyl-ethyl-carbamic acid tert-butyl ester.

Workup

  1. customThe temperature is kept below 40° C. with an cold water bath
  2. extractionextracted with TBME
  3. washThe organic layer is washed extensively with water
  4. concentrationconcentrated under reduced pressure
  5. distillationdistilled at 0.3 mmHg, bp. 38-39°

Sources & evidence

ORD record
ord-aa9d1e1005a04aeb8d27e721522c3dc3
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

Loading…