Hydrochloric Acid → HCID 15390882, compound

HRID 650984Notes

Reaction equation

HRID 650984 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=1.[H-].[Na+].Cl.[O:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29]Cl)[CH2:24][CH2:23]1.Cl>O1CCOCC1.C(O)C>[O:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:9]=2)[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 77919279349-24-9

Product 1

HCID 15390882HCID 15390882, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
27.5 °C

Procedure

2.38 g of 5-(2-hydroxyphenyl)-3-phenyl-1,2,4-oxadiazole are dissolved in 100 ml of anhydrous dioxane and stirred with 0.3 g of 80% sodium hydride suspension in oil for 15 minutes at 25-30° C. To this solution is added 75 ml of absolute dioxane, mixed with 3.72 g of 2-(morpholino)ethylchloride hydrochloride and 0.6 g of 80% sodium hydride suspension in oil. This solution is also stirred for 15 minutes at 25-30° C. The combined solutions are heated to 100° C. for 6 hours and then concentrated by evaporation in vacuo. The residue is mixed with water and 20 ml of 1N sodium hydroxide solution and extracted with ethyl acetate. The organic phase is dried over sodium sulphate, the solvent is distilled off in vacuo and the residue is chromatographed on silica gel with ethyl acetate/isopropanol (70:30, mixed with 1.5% of a 25% ammonia solution). The base thus obtained is dissolved in anhydrous ethanol, acidified with ethereal HCl and precipitated with diethyl ether. The residue is recrystallised from anhydrous ethanol and diethylether. Yield: 1.9 g (49% of theory). m.p.: 194-195° C.

Workup

  1. temperatureThe combined solutions are heated to 100° C. for 6 hours
  2. concentrationconcentrated by evaporation in vacuo
  3. additionThe residue is mixed with water and 20 ml of 1N sodium hydroxide solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. distillationthe solvent is distilled off in vacuo
  7. customthe residue is chromatographed on silica gel with ethyl acetate/isopropanol (70:30
  8. additionmixed with 1.5% of a 25% ammonia solution)
  9. customThe base thus obtained
  10. customprecipitated with diethyl ether
  11. customThe residue is recrystallised from anhydrous ethanol and diethylether

Sources & evidence

ORD record
ord-8add4c1e5cec4345a83ead4c55c33e97
Source dataset
uspto-grants-2001_08
Patent number
US06277872B1

Reaction notes

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