Chloroform → HCID 136399316, compound

HRID 2164365Notes

Reaction equation

HRID 2164365 reaction equation
C(Cl)(Cl)Cl.[CH:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18](=[O:20])[C:17]([C:21](=O)[CH2:22][CH3:23])=[C:16]([OH:25])[CH2:15]2)=[CH:10][CH:9]=1)=[O:6].[CH2:26]([O:28][NH2:29])[CH3:27]>C(O)C>[CH2:26]([O:28][N:29]=[C:21]([C:17]1[C:18](=[O:20])[CH2:19][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([NH:7][CH:5]=[O:6])=[CH:9][CH:10]=2)[CH2:15][C:16]=1[OH:25])[CH2:22][CH3:23])[CH3:27]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 69357Hydroxylamine, O-ethyl-HCID 178458869HCID 178458869, compound

Product 1

HCID 136399316HCID 136399316, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into 25 ml of chloroform was dissolved 1.3 g of 5-(4-formamidophenyl)-3-hydroxy-2-propionyl-2-cyclohexen-1-one and to the solution was added 1.0 g of ethoxyamine and 5 ml og ethanol. The mixture was kept for 3 hours in a water bath having 40° C. and the reacting solution was washed with a dilute hydrochoric acid solution and water. The solution was extracted with 15 ml of aqueous solution containing 5% of sodium hydroxide and to the alkaline solution was added a dilute hydrochloric acid solution and the crystal sedimented was extracted with chloroform. The solution was washed with water and to the solution was added anhydrous magnesium sulfate and a small amount of active carbon. And then, the mixture was agitated and filtered and the filtrate solution was concentrated. Ethyl ether was added in the residue and the crystal sedimented was collected with a filtering step and 1.0 g of desired compound was obtained. It was in the form of colorless crystals having a melting point of 111°-113.5° C.

Workup

  1. customhaving 40° C.
  2. washthe reacting solution was washed with a dilute hydrochoric acid solution and water
  3. extractionThe solution was extracted with 15 ml of aqueous solution
  4. additioncontaining 5% of sodium hydroxide
  5. additionto the alkaline solution was added a dilute hydrochloric acid solution
  6. extractionthe crystal sedimented was extracted with chloroform
  7. washThe solution was washed with water and to the solution
  8. additionwas added anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate solution was concentrated
  11. additionEthyl ether was added in the residue
  12. customthe crystal sedimented was collected with a filtering step

Sources & evidence

ORD record
ord-fb8a4706e24d44fb80d59d38b31afbc8
Source dataset
uspto-grants-1985_03
Patent number
US04504305

Reaction notes

Loading…