Hydrochloric Acid → AN-651/40768841

HRID 2418716Notes

Reaction equation

HRID 2418716 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][C:2]1=[O:12].P(Cl)(Cl)(Cl)(Cl)[Cl:14].[ClH:19]>C1(C)C(C)=CC=CC=1>[Cl:19][C:3]1([Cl:14])[CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:1][C:2]1=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachloride2×HCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 7311798AN-651/40768841

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (48.3 g, see Briggs et al., J. Chem. Soc. 1937, 456), phosphorus pentachloride (188 g), and xylene (1300 ml) was heated with stirring under an atmosphere of nitrogen to 90° (oil bath temperature) during 30 min with pauses at 30° (to allow the phosphorus pentachloride to dissolve) and at 50°. There was a copious evolution of hydrogen chloride. The temperature was maintained at 90° for 30 minutes. The reaction mixture was filtered while hot to remove a small amount of suspended solid, and the filtrate was evaporated under reduced pressure until all the solvent was removed. The residue was added with stirring to saturated aqueous sodium carbonate (100 ml). The product was filtered after the solidification process was complete, then slurried in ethanol (150 ml), filtered, washed with ethanol (50 ml) and ether (50 ml) and dried to give 3,3-dichloro-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 185°-187°.

Workup

  1. temperaturewas heated
  2. dissolutionto dissolve) and at 50°
  3. temperatureThe temperature was maintained at 90° for 30 minutes
  4. filtrationThe reaction mixture was filtered while hot
  5. customto remove a small amount of suspended solid
  6. customthe filtrate was evaporated under reduced pressure until all the solvent
  7. customwas removed
  8. additionThe residue was added
  9. stirringwith stirring to saturated aqueous sodium carbonate (100 ml)
  10. filtrationThe product was filtered after the solidification process
  11. filtrationfiltered
  12. washwashed with ethanol (50 ml) and ether (50 ml)
  13. customdried

Sources & evidence

ORD record
ord-210cf78a69f944c98af33305ded002f4
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

Loading…