Acetic Acid → HCID 86743699, compound

HRID 330325Notes

Reaction equation

HRID 330325 reaction equation
[F:1][C:2]([F:27])([F:26])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[CH:16]=[CH:17][C:18]3[O:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19]=3[CH:25]=2)=O)=[CH:9][CH:8]=1)(=[O:5])=[O:4].O.[NH2:29][NH2:30].C(O)(=O)C>C(O)C>[F:1][C:2]([F:27])([F:26])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:29][NH2:30])[C:15]2[CH:16]=[CH:17][C:18]3[O:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19]=3[CH:25]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 14795414HCID 14795414, compound

Product 1

HCID 86743699HCID 86743699, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.6 grams (0.004 mole) of (4-trifluoromethylsulfonyloxyphenyl)(2,3-dihydro-2,2-dimethylbenzofuran-5-yl) ketone in 75 mL of ethanol was stirred, and 0.6 mL (0.0121 mole) of hydrazine hydrate followed by 0.5 mL of acetic acid were both added via syringe. Upon completion of addition the reaction mixture was heated at reflux for 7 hours and then was allowed to cool to ambient temperature where it was stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was stirred with diethyl ether and water. The mixture was placed in a separatory funnel, and the layers were separated. The organic layer was washed with aqueous 10% sodium hydroxide solution, two portions of water, and with a saturated, aqueous solution of sodium chloride. The organic layer was concentrated under reduced pressure to yield 1.6 grams of (4-trifluoromethylsulfonyloxyphenyl)(2,3-dihydro-2,2-dimethylbenzofuran-5-yl) ketone hydrazone as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionboth added via syringe
  2. additionUpon completion of addition the reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for 7 hours
  5. stirringwas stirred for 18 hours
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. stirringthe residue was stirred with diethyl ether and water
  8. customThe mixture was placed in a separatory funnel
  9. customthe layers were separated
  10. washThe organic layer was washed with aqueous 10% sodium hydroxide solution, two portions of water
  11. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d756ae43de224b69b920525ef066ada6
Source dataset
uspto-grants-1990_01
Patent number
US04895871

Reaction notes

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