Sodium hydride → HCID 21548647, compound

HRID 1605107Notes

Reaction equation

HRID 1605107 reaction equation
[H-].[Na+].C1(NN)C=CC=CC=1.C(=O)C.C1(C(Cl)=O)CCCCC1.Cl.[CH:24]1([C:30]([N:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)N)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[CH2:40]1[CH:46]([C:47]([OH:49])=[O:48])[CH2:45][CH2:44][C:42](=O)[CH2:41]1>O.C(O)(=O)C.CN(C)C=O>[CH:24]1([C:30]([N:32]2[C:42]3[CH2:41][CH2:40][CH:46]([C:47]([OH:49])=[O:48])[CH2:45][C:44]=3[C:39]3[C:34]2=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

9

Reactant 5

HCID 24758Sodium hydrideHCID 75938Cyclohexanecarbonyl chlorideHCID 1927304-Oxocyclohexanecarboxylic acidHCID 21510619HCID 21510619, compoundHCID 21548394HCID 21548394, compound

Product 1

HCID 21548647HCID 21548647, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 3.88 g. of sodium hydride in 100 ml. of dimethylformamide was added portionwise 20 g. of acetaldehyde phenylhydrazine, stirring was continued for 2 hours, 22 g. of cyclohexanecarbonyl chloride was added dropwise, stirring was continued for three hours and the reaction mixture was then poured into ice water containing acetic acid. The aqueous mixture was extracted with ether and the ether extract was washed with water, dried and evaporated to dryness. The residue was taken up in absolute ethyl alcohol and ether, hydrogen chloride in ethyl alcohol was added, and the solution was allowed to stand 1 hour, chilled, and evaporated to dryness under reduced pressure. The residue was triturated with ethyl acetate and the resulting solid was filtered to yield 9.2 g. of 1-cyclohexanecarbonyl-1-phenylhydrazine hydrochloride; m.p. 170°-172°C. This was combined with 5.5 g. of cyclohexanone-4-carboxylic acid in 100 ml. of glacial acetic acid and the mixture was heated at the boiling point for 1 hour, diluted with 50 ml. of water and chilled. The resulting precipitate was collected by filtration, washed with 75% acetic acid in water and dried to yield 3.9 g. of the title compound; m.p. 157°-159°C.

Workup

  1. additionTo a stirred mixture of 3.88 g
  2. waitwas continued for three hours
  3. extractionThe aqueous mixture was extracted with ether
  4. extractionthe ether extract
  5. washwas washed with water
  6. customdried
  7. customevaporated to dryness
  8. additionether, hydrogen chloride in ethyl alcohol was added
  9. waitto stand 1 hour
  10. temperaturechilled
  11. customevaporated to dryness under reduced pressure
  12. customThe residue was triturated with ethyl acetate
  13. filtrationthe resulting solid was filtered
  14. customto yield 9.2 g
  15. additiondiluted with 50 ml
  16. filtrationThe resulting precipitate was collected by filtration
  17. washwashed with 75% acetic acid in water
  18. customdried
  19. customto yield 3.9 g

Sources & evidence

ORD record
ord-fdc8ec4b791f4eee9e5d05e8520a695d
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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