HCID 21249781, compound → HCID 21249765, compound

HRID 2287927Notes

Reaction equation

HRID 2287927 reaction equation
[C:1]([O:6][CH2:7][CH2:8][O:9][C:10](=[O:24])[NH:11][C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[C:14]([N+:21]([O-])=O)[CH:13]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[H][H]>[C].[Pd].C(O)C>[C:1]([O:6][CH2:7][CH2:8][O:9][C:10](=[O:24])[NH:11][C:12]1[CH:13]=[C:14]([NH2:21])[CH:15]=[C:16]([NH2:18])[CH:17]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 21249781HCID 21249781, compound2×HCID 178418361HCID 178418361, compound4×

Product 1

HCID 21249765HCID 21249765, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

4.8 g of 5% palladium carbon, 48.0 g (0.141 mol) of 2-(3,5-dinitrophenylcarbamoyloxy)ethyl isobutyrate (compound 8) and 700 ml of ethanol were placed in a 5-l autoclave equipped with a thermocouple thermometer and a mixing blade, and the autoclave was sealed. The atmosphere inside the autoclave was replaced by hydrogen and the hydrogen pressure was raised to 5 kg/cm2. The autoclave contents were stirred at room temperature (20° C.). Ten minutes later, the autoclave inside temperature rose to 34° C. and the autoclave inside pressure dropped to 1 kg/cm2. Then, hydrogen was introduced to raise the pressure to 5 kg/cm2, and stirring was continued. 20 minutes later, the temperature became 30° C. and the pressure dropped to 2.5 kg/cm2. Hydrogen was again introduced to raise the pressure to 5 kg/cm2, and stirring was continued. Since the temperature began to drop and the pressure became constant (3 kg/cm2), stirring was continued for 70 minutes (the temperature dropped to 23° C.). The atmosphere inside the autoclave was replaced by nitrogen, and the autoclave contents were taken out and filtered to remove palladium carbon. The filtrate was concentrated by the use of an evaporator. The resulting concentrate was placed under reduced pressure by the use of a rotary pump to distil off the solvent to obtain 2-(3,5-diaminophenylcarbamoyloxy)ethyl isobutyrate (compound 9) as a brown viscous liquid. Yield: 33.7 g (85%)

Workup

  1. customequipped with a thermocouple thermometer
  2. customa mixing blade, and the autoclave was sealed
  3. customTen minutes
  4. customrose to 34° C.
  5. additionthe autoclave inside pressure dropped to 1 kg/cm2
  6. temperatureto raise the pressure to 5 kg/cm2
  7. stirringstirring
  8. custom20 minutes
  9. custombecame 30° C.
  10. additionthe pressure dropped to 2.5 kg/cm2
  11. temperatureto raise the pressure to 5 kg/cm2
  12. stirringstirring
  13. stirringstirring
  14. addition(the temperature dropped to 23° C.)
  15. filtrationfiltered
  16. customto remove palladium carbon
  17. concentrationThe filtrate was concentrated by the use of an evaporator
  18. concentrationThe resulting concentrate
  19. customto distil off the solvent

Sources & evidence

ORD record
ord-d8a0246fd05f4932be85f61aa9441573
Source dataset
uspto-grants-2000_07
Patent number
US06087006

Reaction notes

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