Hydrochloric Acid → HCID 20338056, compound

HRID 1395754Notes

Reaction equation

HRID 1395754 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:16]([CH3:20])[C:17](O)=[O:18].S(Cl)(Cl)=O.O.[NH3:26].Cl>C1C=CC=CC=1.N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:16]([CH3:20])[C:17]([NH2:26])=[O:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 12896473Azane;hydrateHCID 20338050HCID 20338050, compound

Product 1

HCID 20338056HCID 20338056, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

To 132 mg of 2-(10,11-dihydro dibenzo[b,f]oxepin-2-yl)-propionic acid in 2 ml of benzene were added 0.6 ml of thionyl chloride and three drops of pyridine and the mixture was stirred at room temperature for 1 hour, then refluxed with stirring for 1 hour. The solvent was distilled off to obtain the residue, which was dissolved in 2 ml of chloroform and the resulting solution was added to 2 ml of 28% ammonia water. The mixture was stirred at room temperature for 3 hours. The reaction mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with 1N-sodium hydroxide solution, then saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain yellowish brown oil, which was chromatographed over silica gel, eluted with chloroform/methanol (200/1). The eluate was crystallized from benzene-n-hexane to give 115 mg of 2-(10,11-dihydro dibenzo[b,f]oxepin-2-yl)-propionamide as pale yellow crystals having a melting point of 122.5°-123° C.

Workup

  1. temperaturerefluxed
  2. stirringwith stirring for 1 hour
  3. distillationThe solvent was distilled off
  4. customto obtain the residue, which
  5. stirringThe mixture was stirred at room temperature for 3 hours
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with 1N-sodium hydroxide solution
  8. dry with materialsaturated sodium chloride solution and dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customto obtain yellowish brown oil, which
  11. customwas chromatographed over silica gel
  12. washeluted with chloroform/methanol (200/1)
  13. customThe eluate was crystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-0e089f8f7d1b43099be32076ad73966a
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

Loading…