Triethylamine → HCID 14098128, compound

HRID 569474Notes

Reaction equation

HRID 569474 reaction equation
O=[C:2]1[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][C:3]1([C:12](OCC)=[O:13])[CH2:4]3)[CH2:8]2.Cl.[Cl:18][C:19]1[CH:20]=[C:21]([NH:25][NH2:26])[CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C>C(O)C>[Cl:18][C:19]1[CH:20]=[C:21]([N:25]2[N:26]=[C:2]3[CH:9]4[CH2:10][CH:5]5[CH2:4][C:3]3([CH2:11][CH:7]([CH2:6]5)[CH2:8]4)[C:12]2=[O:13])[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 12440626HCID 12440626, compound

Product 1

HCID 14098128HCID 14098128, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-oxoadamantane-1-carboxylate (5) (1.0 g, 4.5 mmol) and 3-chlorophenylhydrazine hydrochloride (3.6 g, 20 mmol) in 40 ml of ethanol is added triethylamine (2.0 g, 20 mmol). The reaction mixture is stirred at room temperature under a nitrogen atmosphere for 20 hours, then heated to reflux for 2 hours. After cooling to ambient temperature, the solvent is removed under reduced pressure and the crude residue solid is dissolved in 30 ml of methylene chloride. The organic extract is washed with 25 ml of diluted hydrochloric acid to remove the excess of 3-chlorophenylhydrazine, then dried over anhydrous magnesium sulfate. The solvent is evaporated to leave the title compound (6) as a dark-colored, viscous oil which is flash-chromatographed on silica gel using ether-pentane (2:8) as the eluent. Subsequent recrystallization from methanol provides the pure product as pale yellow needles melting at 119.5°-120.5° C. Anal. Calcd for C17H17ClN2O: C, 67.88; H, 5.70; N, 9:31; Cl, 11.79. Found: C, 67.54; H, 5.75; N, 9.12; Cl, 11.86.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling to ambient temperature
  4. customthe solvent is removed under reduced pressure
  5. dissolutionthe crude residue solid is dissolved in 30 ml of methylene chloride
  6. extractionThe organic extract
  7. washis washed with 25 ml of diluted hydrochloric acid
  8. customto remove the excess of 3-chlorophenylhydrazine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent is evaporated

Sources & evidence

ORD record
ord-c897e3130a3143fd935a427201abdb8d
Source dataset
uspto-grants-1988_03
Patent number
US04732909

Reaction notes

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