Dimethyl Carbonate → methyl N-[6-(methoxycarbonylamino)hexyl]carbamate

HRID 1618323

Reaction equation

HRID 1618323 reaction equation
[C:1](=[O:6])([O:4][CH3:5])OC.[N+:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N+:16]([O-])=O)([O-])=O>>[CH3:5][O:4][C:1]([NH:7][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:1]([O:4][CH3:5])=[O:6])=[O:6]

Participants

3

Reactant 2

HCID 12021Dimethyl CarbonateHCID 2206561,6-Dinitrohexane

Product 1

HCID 235165methyl N-[6-(methoxycarbonylamino)hexyl]carbamateYield 85%

Procedure

In a reinforced glass reactor with a capacity of 5 ml 2 ml of dimethyl carbonate and 150 mg of 1,6-dinitrohexane and 100 mg of Au/CeO2 (1 wt % gold relative to cerium) are introduced. The reactor is closed and purged with N2 to remove oxygen from the solution. Then the reactor is charged at 15 bars of hydrogen and immersed in a silicone bath preheated at 90° C. The suspension is magnetically stirred for 8 hrs. After this time, the reactor is discharged at atmospheric pressure, opened and the mixture is filtered. A gas chromatography analysis revealed the presence of 1,6-bis (methoxycarbonylamino) hexane in an 85% yield.

Workup

  1. customThe reactor is closed
  2. custompurged with N2
  3. customto remove oxygen from the solution
  4. additionThen the reactor is charged at 15 bars of hydrogen
  5. customimmersed in a silicone bath
  6. custompreheated at 90° C
  7. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-f34b0b06e50b4d638683136a9424c064
Source dataset
uspto-grants-2014_07
Patent number
US08765993B2

Linked notes

Loading…