Toluene → Ethyl allyl(2,2-dimethoxyethyl)carbamate

HRID 345795Notes

Reaction equation

HRID 345795 reaction equation
[H-].[Na+].[C:3]1([CH3:9])[CH:8]=CC=CC=1.[CH3:10][O:11][CH:12]([O:20][CH3:21])[CH2:13][NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18].C(Br)C=C>O>[CH2:9]([N:14]([CH2:13][CH:12]([O:11][CH3:10])[O:20][CH3:21])[C:15](=[O:19])[O:16][CH2:17][CH3:18])[CH:3]=[CH2:8]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 10921057Ethyl 2,2-dimethoxyethylcarbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

20 g of sodium hydride (80% strength in paraffin oil) are initially introduced into 500 ml of toluene and 89 g (0.5 mol) of ethyl N-(2,2-dimethoxyethyl)-carbamate are added dropwise at 80° C. The mixture is stirred at 80° C. for one hour and 73 g (0.6 mol) of allyl bromide are then added dropwise in the course of three hours. The mixture is stirred at 80° C. overnight, the salts are dissolved with water and the organic phase is separated off. The aqueous phase is extracted with toluene, the organic phases are dried over potassium carbonate and concentrated and the residue is distilled.

Workup

  1. additionare added dropwise at 80° C
  2. stirringThe mixture is stirred at 80° C. overnight
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted with toluene
  5. dry with materialthe organic phases are dried over potassium carbonate
  6. concentrationconcentrated
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-cf20850c7e40415d88270a1b22aabd7e
Source dataset
uspto-grants-1991_10
Patent number
US05059597

Reaction notes

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