Hydrochloric Acid → HCID 20149487, compound

HRID 568973Notes

Reaction equation

HRID 568973 reaction equation
C1(=O)[N:5]([C:6]([C:30]([O:32][CH2:33][CH3:34])=[O:31])([CH2:12][CH2:13][CH:14]([F:29])[CH:15]([N:18]2C(=O)C3=CC=CC=C3C2=O)[CH:16]=[CH2:17])[C:7]([O:9][CH2:10][CH3:11])=[O:8])C(=O)C2=CC=CC=C12.O1CCOCC1.C(O)C.Cl.C(O)C.N>C(O)C>[NH2:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH2:12][CH2:13][CH:14]([F:29])[CH:15]([NH2:18])[CH:16]=[CH2:17])[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 20149438HCID 20149438, compoundHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 22560076Dioxan ethanol

Product 1

HCID 20149487HCID 20149487, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

The foregoing compound 22 (17.5 g, 31.8 mmoles) and a 1M solution of N2H4.H2O in dioxane/ethanol 4:1 (35 mL, 2 equivalents) are stirred and heated at about 90° C. After 3 hours, a yellow precipitate is formed, and the mixture is allowed to cool to room temperature. The precipitate is filtered and the filtrate is evaporated to yield an oil. The oil and the precipitate are united and heated with ethanol (310 mL) and conc. HCl (18.6 mL) at 90° C. for 3 hours. After cooling, phthalhydrazide is filtered and the solution is evaporated. Dissolving in water, filtration, evaporation, dissolving in ethanol, evaporating again and drying (oil pump) yields a yellow foam: 11.5 g (about 100%). Thin layer chromatography (ethanol/ammonia 80/20) shows a second spot (presumably some ester cleaved). The compound 23 is utilized for the next step without further purification.

Workup

  1. customa yellow precipitate is formed
  2. temperatureto cool to room temperature
  3. filtrationThe precipitate is filtered
  4. customthe filtrate is evaporated
  5. customto yield an oil
  6. temperatureAfter cooling
  7. filtrationphthalhydrazide is filtered
  8. customthe solution is evaporated
  9. dissolutionDissolving in water
  10. filtrationfiltration, evaporation
  11. dissolutiondissolving in ethanol
  12. customevaporating again
  13. customdrying (oil pump)
  14. customyields a yellow foam
  15. customThe compound 23 is utilized for the next step without further purification

Sources & evidence

ORD record
ord-855a897586584be5a0c309f2878ebce1
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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