Diethyl Ether → HCID 22934672, compound

HRID 2104419Notes

Reaction equation

HRID 2104419 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[O:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[C:16](=[O:19])([O-])O.[Na+].[CH2:21](OCC)[CH3:22]>>[C:15]1([O:11][C:16]([NH:10][NH:9][C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)=[O:19])[CH:22]=[CH:21][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 22934672HCID 22934672, compound

Procedure

(4-Chlorophenyl)hydrazine hydrochloride (3.00 g) was added to a mixture of tetrahydrofuran (50 mL), diethyl ether (50 mL), and saturated aqueous sodium hydrogencarbonate. The organic layer was separated, followed by drying over sodium sulfate anhydrate and concentrating, to thereby give (4-chlorophenyl)hydrazine as a brown solid. The solid was dissolved in benzene (15 mL), and the solution was heated under reflux. Under refluxing, diphenyl carbonate (5.22 g) dissolved in benzene (8.0 mL) was added dropwise thereto over 30 minutes or more. The mixture was refluxed for 19 hours, allowed to cool to room temperature, and concentrated. Benzene (15 mL) was added thereto, and the mixture was slurried by ultrasonic wave. Hexane (50 mL) was added thereto, and the resultant mixture was stirred for 30 minutes. The insoluble material was recoverd by filtration, followed by drying, to thereby give the title compound (1.05 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialby drying over sodium sulfate anhydrate
  3. concentrationconcentrating
  4. dissolutionThe solid was dissolved in benzene (15 mL)
  5. temperaturethe solution was heated
  6. temperatureunder reflux
  7. temperatureUnder refluxing
  8. dissolutiondiphenyl carbonate (5.22 g) dissolved in benzene (8.0 mL)
  9. additionwas added dropwise
  10. waitover 30 minutes or more
  11. temperatureThe mixture was refluxed for 19 hours
  12. concentrationconcentrated
  13. additionBenzene (15 mL) was added
  14. additionHexane (50 mL) was added
  15. filtrationThe insoluble material was recoverd by filtration
  16. customby drying

Sources & evidence

ORD record
ord-a9df1d3e13ac4e6c8b43569fb054a2ae
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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