Carbamic acid, ethyl ester → Diethyl toluene-2,4-dicarbamate

HRID 128465

Reaction equation

HRID 128465 reaction equation
[NH2:1][C:2]([O:4][CH2:5][CH3:6])=[O:3].[Mn]([O-])(=O)(=O)=O.[K+].C[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=1[CH3:20]>>[CH2:5]([O:4][C:2]([NH:1][C:18]1[CH:17]=[C:16]([NH:1][C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH:15]=[CH:14][C:19]=1[CH3:20])=[O:3])[CH3:6]

Participants

4

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 7237O-XyleneHCID 516875Potassium Permanganate

Product 1

HCID 343975Diethyl toluene-2,4-dicarbamate

Conditions

Temperature
80 °C

Procedure

10 g of the urethane which had previously been treated in this way were dissolved in 60 g o-xylene. The solution is heated to 80° C. and mixed with 2 g of a 2%, by weight, aqueous potassium permanganate solution. The mixture was stirred intensely for 30 minutes at 80° C. The hot organic phase was then separated from the solid and aqueous constituents. The organic phase was concentrated by distilling off a proportion of the xylene to half of its original volume, and the purified 2,4-bis-(ethoxycarbonylamino)-toluene was obtained in a virtually quantitative yield from the concentrated solution by crystallization.

Workup

  1. customThe hot organic phase was then separated from the solid and aqueous constituents
  2. concentrationThe organic phase was concentrated
  3. distillationby distilling off a proportion of the xylene to half of its original volume

Sources & evidence

ORD record
ord-2434c732e1b74e2095af672870efccea
Source dataset
uspto-grants-1981_03
Patent number
US04259511

Linked notes

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