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

HRID 981103Notes

Reaction equation

HRID 981103 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:5].[H-].[Na+].[H][H].[CH2:18](Cl)[CH:19]=[CH2:20]>C1(C)C=CC=CC=1>[CH2:20]([N:6]([CH:4]([CH3:5])[CH:3]([O:2][CH3:1])[O:12][CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 7850Allyl chlorideHCID 24758Sodium hydrideHCID 15069987N-(1,1-dimethoxyprop-2-yl)urethaneHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

131 g (0.686 mol) of N-(1,1-dimethoxyprop-2-yl)urethane are added dropwise to 25 g of sodium hydride (80% strength) in 700 ml of absolute toluene at 90° C. When the evolution of hydrogen has ended, 61.2 g (0.8 mol) of allyl chloride are added dropwise at 90° C. and the mixture is stirred overnight at 90° C. The sodium chloride which has precipitated out is dissolved with water, the organic phase is separated off, dried over K2CO3 and concentrated and the residue is distilled.

Workup

  1. customThe sodium chloride which has precipitated out
  2. dissolutionis dissolved with water
  3. customthe organic phase is separated off
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-6f69106455d1494da81173f22870e22c
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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