Hydrochloric Acid → HCID 53950580, compound

HRID 1636375Notes

Reaction equation

HRID 1636375 reaction equation
[C:1]12([CH2:11][CH2:12][O:13][NH:14][C:15]([C:17]3[CH:25]=[CH:24][C:20](C(O)=O)=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)(Cl)=O.Cl.[NH2:31][OH:32].[C:33](=[O:36])(O)[O-].[Na+].[OH-].[Na+].Cl>C(Cl)(Cl)Cl.N1C=CC=CC=1.C1COCC1>[C:1]12([CH2:11][CH2:12][O:13][NH:14][C:15]([C:17]3[CH:25]=[CH:24][C:20]([C:33]([NH:31][OH:32])=[O:36])=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 19351149HCID 19351149, compound

Product 1

HCID 53950580HCID 53950580, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the compound obtained in step A (3 g, 8.7 mmoles) in chloroform (50 ml), was added with thionyl chloride (1.2 ml, 17.4 mmoles) and 3 drops of pyridine. The reaction mixture was refluxed for 5 hours, then evaporated to dryness. The residue was redissolved in chloroform and re-evaporated to dryness three times. The resulting 4-[2-(adamant-1-yl)ethoxycarbamoyl]benzoyl chloride was dissolved in THF (50 ml) and the solution was added slowly to a solution of hydroxylamine hydrochloride (0.7 g, 10.4 mmoles) and sodium bicarbonate (0,7 g, 8.7 mmoles) in 1N sodium hydroxide (10.4 ml, 10.4 mmoles) and THF (20 ml), then stirred at room temperature for 8 hours, acidified with 1N HCl, and THF was evaporated in the cold. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over anhydrous sodium sulfate and the solvent was evaporated off. The resulting crude was treated with warm ethyl ether and filtered to give 1.5 g of the title compound (48% yield); m.p.=198-200° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. customevaporated to dryness
  3. dissolutionThe residue was redissolved in chloroform
  4. customre-evaporated to dryness three times
  5. dissolutionThe resulting 4-[2-(adamant-1-yl)ethoxycarbamoyl]benzoyl chloride was dissolved in THF (50 ml)
  6. customwas evaporated in the cold
  7. extractionThe aqueous phase was extracted with ethyl acetate
  8. dry with materialthe combined organic phases were dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated off
  10. additionThe resulting crude was treated with warm ethyl ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-5c487dea114e4d3f9bc97c694d6eaf6a
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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