HCID 21249770, compound → HCID 21249775, compound

HRID 2287930Notes

Reaction equation

HRID 2287930 reaction equation
[C:1]([O:6][CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[C:15]([N+:22]([O-])=O)[CH:14]=1)=[O:11])(=[O:5])[CH:2]([CH3:4])[CH3:3].[H][H]>[C].[Pd].C(O)C>[C:1]([O:6][CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([NH2:19])[CH:16]=[C:15]([NH2:22])[CH:14]=1)=[O:11])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 21249770HCID 21249770, compound2×HCID 178418361HCID 178418361, compound4×

Product 1

HCID 21249775HCID 21249775, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
17 °C

Procedure

8.3 g of 5% palladium carbon, 83.0 g (0.244 mol) of 2-(3,5-dinitrophenylureido)ethyl isobutyrate (compound 12) and 800 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 (17° C.). Ten minutes later, the autoclave inside temperature rose to 43° 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. Ten minutes later, the temperature became 58° C. and the pressure dropped to 1 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 (4.5 kg/cm2), stirring was continued for 60 minutes (the temperature dropped to 26° 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, whereby a solid was separated. The solid was recrystallized from 300 ml of butanol to obtain 2-(3,5-diaminophenylureido)ethyl isobutyrate (compound 13). Yield: 55.0 g (81%) Melting point: 89-90° C.

Workup

  1. customequipped with a thermocouple thermometer
  2. customa mixing blade, and the autoclave was sealed
  3. customTen minutes
  4. customrose to 43° C.
  5. additionthe autoclave inside pressure dropped to 1 kg/cm2
  6. temperatureto raise the pressure to 5 kg/cm2
  7. stirringstirring
  8. customTen minutes
  9. custombecame 58° C.
  10. additionthe pressure dropped to 1 kg/cm2
  11. temperatureto raise the pressure to 5 kg/cm2
  12. stirringstirring
  13. stirringstirring
  14. addition(the temperature dropped to 26° C.)
  15. filtrationfiltered
  16. customto remove palladium carbon
  17. concentrationThe filtrate was concentrated by the use of an evaporator, whereby a solid
  18. customwas separated
  19. customThe solid was recrystallized from 300 ml of butanol

Sources & evidence

ORD record
ord-e5361f40c2ba48dba3a0cc70f140077d
Source dataset
uspto-grants-2000_07
Patent number
US06087006

Reaction notes

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