Toluene → N-Allyl-N-(1,1-dimethoxyprop-2-yl)-urethane

HRID 1460765Notes

Reaction equation

HRID 1460765 reaction equation
[CH2:1]([NH:4][CH:5]([CH3:11])[CH:6]([O:9][CH3:10])[O:7][CH3:8])[CH:2]=[CH2:3].C1(C)C=CC=CC=1.[OH-].[Na+].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>O>[CH2:1]([N:4]([CH:5]([CH3:11])[CH:6]([O:9][CH3:10])[O:7][CH3:8])[C:22](=[O:23])[O:24][CH2:25][CH3:26])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 19100951HCID 19100951, compound

Product 1

HCID 15069988N-Allyl-N-(1,1-dimethoxyprop-2-yl)-urethane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

125 g (0.785 mol) of allyl-(1,1-dimethoxyprop-2-yl)amine are initially introduced into 400 ml of toluene, a solution of 40 g of sodium hydroxide in 200 ml of water is added, the mixture is cooled in an ice-bath to 0° C. and 95 g (0.876 mol) of ethyl chloroformate are added dropwise. The mixture is then stirred for 3 hours at room temperature, and the aqueous phase is separated off and extracted twice using 100 ml of toluene each time. The extracts are dried over potassium carbonate and concentrated, and the residue is distilled.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted twice
  3. dry with materialThe extracts are dried over potassium carbonate
  4. concentrationconcentrated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-73099fecb80f468a9a43e0cb12957f27
Source dataset
uspto-grants-1991_12
Patent number
US05071999

Reaction notes

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