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

HRID 2255696Notes

Reaction equation

HRID 2255696 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH:4]([NH:6][C:7](=[O:11])[O:8][CH2:9][CH3:10])[CH3:5].[OH-].[K+].[C:16]1(C)[CH:21]=CC=C[CH:17]=1.C(Br)C=C>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[CH2:21]([N:6]([CH:4]([CH3:5])[CH:3]([O:2][CH3:1])[O:12][CH3:13])[C:7](=[O:11])[O:8][CH2:9][CH3:10])[CH:16]=[CH2:17]

Participants

7

Reactant 4

HCID 1140TolueneHCID 7841Allyl bromide2×HCID 14797Potassium HydroxideHCID 15069987N-(1,1-dimethoxyprop-2-yl)urethane

Product 1

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

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

151 g (0.79 mol) of ethyl N-(1,1-dimethoxyprop2-yl)-carbamate, 175 g of powdered potassium hydroxide and 2.8 g of triethylbenzylammonium chloride are initially introduced into 750 ml of toluene and 94 g (0.777 mol) of allyl bromide are added dropwise at room temperature. After stirring overnight at room temperature, a further 10 g (82.6 mmol) of allyl bromide are added dropwise and the mixture is stirred for one day at room temperature. Water is added until all salts have gone into solution, and the aqueous phase is separated off and extracted twice with 150 ml of toluene each time. The extracts are dried over K2CO3 and concentrated, and the residue is distilled.

Workup

  1. additionare added dropwise at room temperature
  2. stirringthe mixture is stirred for one day at room temperature
  3. customthe aqueous phase is separated off
  4. extractionextracted twice with 150 ml of toluene each time
  5. dry with materialThe extracts are dried over K2CO3
  6. concentrationconcentrated
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-9b0657a5b3aa4f2ca2cb3943d3287746
Source dataset
uspto-grants-1993_08
Patent number
US05241076

Reaction notes

Loading…