Water → HCID 15592711, compound

HRID 2414048Notes

Reaction equation

HRID 2414048 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[CH2:8]([N:13]([C:19]([O:21][CH2:22][C:23]#[CH:24])=[O:20])[C:14](=[O:18])[C:15](Cl)=[O:16])[C:9]([CH3:12])([CH3:11])[CH3:10].O>C1(C)C=CC=CC=1>[CH2:1]([N:4]([CH2:5][CH:6]=[CH2:7])[C:15](=[O:16])[C:14]([N:13]([CH2:8][C:9]([CH3:11])([CH3:10])[CH3:12])[C:19]([O:21][CH2:22][C:23]#[CH:24])=[O:20])=[O:18])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31279DiallylamineHCID 15592708HCID 15592708, compound

Product 1

HCID 15592711HCID 15592711, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.88 g (0.4 mole) of diallylamine are added dropwise to 5.35 g (0.02 mole) of 97% pure N-neopentyl-N-2-propinyloxycarbonyloxamic acid chloride in 50 ml of toluene. During this addition, the internal temperature is kept at 20° C. by external cooling with ice. When the dropwise addition has ended, 30 ml of water are added, the organic phase is separated off and the latter is washed twice with water, dried over sodium sulphate and finally concentrated in vacuo. 5.5 g (86% of theory) of N,N-diallyl-N'-neopentyl-N'-2-propinyloxycarbonyl-oxalic acid diamide of refractive index nD20 =1.4878 are obtained.

Workup

  1. additionDuring this addition
  2. customis kept at 20° C.
  3. temperatureby external cooling with ice
  4. additionWhen the dropwise addition
  5. customthe organic phase is separated off
  6. washthe latter is washed twice with water
  7. dry with materialdried over sodium sulphate
  8. concentrationfinally concentrated in vacuo

Sources & evidence

ORD record
ord-5b122ad3ac76474b8d9b769313681b6a
Source dataset
uspto-grants-1988_01
Patent number
US04721523

Reaction notes

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