Hydrochloric Acid → HCID 20070461, compound

HRID 981589Notes

Reaction equation

HRID 981589 reaction equation
N12[CH2:11][CH2:10]CCC1C=NCCC2.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=1.[N+](CC)([O-])=[O:27].Cl.[OH-].[Na+].S(=O)(=O)(O)O>C(#N)C.O>[F:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([CH2:20][C:21](=[O:25])[CH:22]([CH3:23])[CH3:24])[C:10]([CH3:11])=[O:27])=[CH:17][CH:18]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 6587NitroethaneHCID 14798Sodium HydroxideHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 537214671-(4-Fluorophenyl)-4-methylpent-1-en-3-one

Product 1

HCID 20070461HCID 20070461, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 7.9 g (0.05 mol) of 1,5-diazabicyclo(5,4,0)undec-5-ene in 50 ml of acetonitrile is added dropwise at 0° C. to a solution of 19.2 g (0.1 mol) of 1-(4-fluorophenyl)-4-methyl-pent-1-en-3-one and 8.6 ml (0.12 mol) of nitroethane in 100 ml of acetonitrile. The mixture is then stirred at room temperature for 3 hours and 100 ml of 0.5 N hydrochloric acid are added. After extraction with methylene chloride, the organic phase is dried using sodium sulphate and concentrated. The oily residue is dissolved in 100 ml of ethanol and a solution of 4.8 g (0.12 mol) of sodium hydroxide in 60 ml of water is added at room temperature. This reaction solution is then added dropwise with ice cooling to a solution of 13.3 ml (0.25 mol) of concentrated sulphuric acid in 100 ml of water. After stirring for 0.5 hours at room temperature, the mixture is diluted with water and extracted several times with ether. The organic phase is washed twice each with 0.5 N hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate, concentrated in vacuo and the residue is chromatographed on silica gel.

Workup

  1. extractionAfter extraction with methylene chloride
  2. customthe organic phase is dried
  3. concentrationconcentrated
  4. dissolutionThe oily residue is dissolved in 100 ml of ethanol
  5. stirringAfter stirring for 0.5 hours at room temperature
  6. extractionextracted several times with ether
  7. washThe organic phase is washed twice each with 0.5 N hydrochloric acid and saturated sodium bicarbonate solution
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated in vacuo
  10. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-f59ad7829d494cef9907d4f4a3b57417
Source dataset
uspto-grants-1991_02
Patent number
US04992462

Reaction notes

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