Allyl bromide → Ethyl allyl(2,2-dimethoxyethyl)carbamate

HRID 2255680Notes

Reaction equation

HRID 2255680 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[CH2:4][NH:5][C:6](=[O:10])[O:7][CH2:8][CH3:9].[OH-].[K+].[CH2:15](Br)[CH:16]=[CH2:17]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C1(C)C=CC=CC=1>[CH2:17]([N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:11][CH3:12])[C:6](=[O:10])[O:7][CH2:8][CH3:9])[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 10921057Ethyl 2,2-dimethoxyethylcarbamate

Product 1

HCID 10943907Ethyl allyl(2,2-dimethoxyethyl)carbamate

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

500 g (2.82 mol) of ethyl N-(2,2-dimethoxyethyl)-carbamate, 625 g of powdered potassium hydroxide and 10 g of triethylbenzylammonium chloride are initially introduced into 2.7 l of toluene and 345 g (2.85 mol) of allyl bromide are added dropwise at room temperature. The mixture is stirred overnight at room temperature, the salts are filtered off with suction, and the filtrate is washed once with saturated sodium chloride solution, dried over potassium carbonate, concentrated and distilled.

Workup

  1. additionare added dropwise at room temperature
  2. filtrationthe salts are filtered off with suction
  3. washthe filtrate is washed once with saturated sodium chloride solution
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-08af20140e064ace816a0f0c845ee824
Source dataset
uspto-grants-1993_08
Patent number
US05241076

Reaction notes

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