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

HRID 981083Notes

Reaction equation

HRID 981083 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-4ba474d874ba48a98878816d6297f6ef
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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